Category: iodides-buliding-blocks

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 108078-14-4, name is 2-Iodo-3-methylbenzoic acid, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 108078-14-4

2-iodo-3-methylbenzoic acid (595 mg, 2.27 mmol) was dissolved in DCM/MeOH=1/1 (5 ml) at 0 C., then TMS-CH2N2 (2M in Et2O, 1.4 ml, 2.8 mmol) was added. After 1.5 hours at RT solvents were evaporated. Yield 630 mg yellow oil. 1HNMR (CDCl3) delta ppm==7.42-7.32 (m, 2H), 7.32-7.25 (m, 1H, under the solvent peak), 2.55 (s, 3H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 108078-14-4.

Reference:
Patent; Stasi, Luigi Piero; Rovati, Lucio Claudio; Artusi, Roberto; Colace, Fabrizio; Mandelli, Stefano; Perugini, Lorenzo; US2014/357653; (2014); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 791642-68-7, name is 4-Bromo-1-iodo-2-methoxybenzene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 791642-68-7, Product Details of 791642-68-7

Step 2: 4-bromo-1-iodo-2-methoxybenzene (647 mg, 2.07 mmol), tert-butyl piperazine-1-carboxylate (350 mg, 1.88 mmol), sodium tert-butoxide (541 mg, 5.6 mmol), Pd2(dba)3 (52 mg, 0.056 mmol) and XantPhos (98 mg, 0.17 mmol) were taken up in toluene (18 mL) under Ar. The reaction mixture was stirred for 18 h and was then heated to 45 C. After an additional 2.5 h, the temperature was increased to 65 C. After an additional 3 h, the reaction mixture was cooled and partitioned between water and EtOAc. The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-25% EtOAc in hexanes) to afford tert-butyl 4-(4-bromo-2-methoxyphenyl)piperazine-1-carboxylate 7.09.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-iodo-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 83171-49-7, name is 3-Chloro-5-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-5-iodoaniline

General procedure: The corresponding pyrazinoic acid (5.0 mmol) was dispersed in dry toluene (20 mL) and mixed with 1.5eq. of thionyl chloride (0.55 mL, 7.5 mmol). The reaction mixture was heated to reflux for approximately 1 h. Next, the excess of thionyl chloride was removed by repeated evaporation with dry toluene under vacuum.The crude acyl chloride was dissolved in dry acetone(20 mL) and added drop-wise to a stirred solution of the corresponding aniline (5.0 mmol) with triethylamine(5.0 mmol) in dry acetone (30 mL). The reaction mixture was stirred at ambient temperature for up to 6 h. The completion of the reaction was monitored by TLC (eluent: hexane/ethyl acetate; r =2 : 1). The crude product adsorbed on silica gel by solvent evaporation was purified by flash chromatography(hexane/ethyl acetate gradient elution).The analytical data of the prepared compounds were fully consistent with the proposed structures and are available in the Supplementary Data.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 83171-49-7.

Reference:
Article; Zitko, Jan; Barbora, Servusova-Vanaskova; Paterova, Pavla; Navratilova, Lucie; Trejtnar, Frantisek; Kunes, Jiri; Dolezal, Martin; Chemical Papers; vol. 70; 5; (2016); p. 649 – 657;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5876-51-7, name is 5-Iodobenzo[d][1,3]dioxole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Iodobenzo[d][1,3]dioxole

[00216] This example demonstrates that palladium catalysts can be activated by treatment with a base prior to their use in promoting the reaction of an organic halide with a dialkoxyborane. In particular, the catalytic activity of PdCl2(dppf).CH2Cl2 can be increased significantly, especially the initial activity, by treatment, in the reaction solvent, with triethylamine prior to the addition of the pinacolborane and substrate. Besides the rate enhancement observed in the formation of the required product boronic acid ester (e.g. pinacol ester of 3,4-methylenedioxyphenylboronic acid) there is a further advantage in the prior activation of the catalyst in that the amount of bi-product formed in the reaction (viz. 1,3-benzodioxole through dehalogenation of the substrate and the pinacol ester of phenylboronic acid in which the phenyl groups are from the catalyst ligand) is significantly reduced. Formation of 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzodioxole [00217] [C00024] [00218] To 24.6 mg PdCl2(dppf).CH2Cl2 in a reaction tube under nitrogen was added 4 ml dioxane and 0.42 ml (3 mmol) triethylamine. The mixture was heated at 80 C. for ca 17 h. The red-orange suspension of PdCl2(dppf).CH2Cl2 dissolved to give a dark red-brown solution. To this solution, at room temperature, was added 0.23 ml (1.5 mmol) pinacolborane and 253 mg (1.02 mmol) 1-iodo-3,4-methylenedioxybenzene. The reaction solution was warmed to 80 C. with stirring for 1 h in an oil bath. The solution remained a dark red-brown in colour. An aliquot (ca. 0.25 ml) of the reaction solution was removed, extracted into ethyl acetate and washed several times with water and brine solution and analysed by gc (fid detector, SGE HT5 capillary column). Apart from a small amount of 1,3-benzodioxole (5% of uncorrected gc peak area) and pinacol ester of phenylboronic acid (3%), the only other product peak in the gc (area of 92%, uncorrected) was that due to the desired arylboronic acid pinacol ester. There was no evidence of biaryl formation. The rate of reaction of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 80 C. with activated catalyst is indicated also in Table 17.1. Table 17.2 shows that side product formation can be reduced still further by carrying out the reaction at 30 C. [TABLE-US-00002] TABLE 17.1 Rate of product formation on reaction* of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 80 C. in which the catalyst, PdCl2(dppf).CH2Cl2, was activated, prior to employment in the reaction, with triethylamine. The concentrations are expressed in area % (uncorrected for response factors) determined by gc analysis of aliquots of the reaction solution taken at selected reaction times. Reaction Time (mins) [C00025] [C00026] [C00027] [C00028] 6 4.4 0.74 54 40 10 4.4 1.0 40 55 15 5.2 2.1 26 66 20 5.9 2.9 16.3 75 25 5.7 2.9 9.2 82 30 6.0 3.2 3.6 87 35 5.9 3.4 1.2 89 40 5.7 3.4 0.7 90 50 5.6 3.4 0 91 180 5.7 3.5 0 91 *Used 25.5 mg of PdCl2(dppf).CH2Cl2. 4 ml dioxane, 0.43 ml (3.0 mmol) triethylamine and warmed to 80 C. for 16 h. Then added 0.23 ml (1.5 mmol) pinacolborane and 247 mg (1.0 mmol) 1-iodo-3,4-methylenedioxybenzene at room temp. before warming the reaction to 80 C. The reaction was quenched at the selected reaction time by addition of the aliquot of reaction solution to a water/ethyl acetate mixture. [TABLE-US-00003] TABLE 17.2 Rate of product formation on reaction* of 1-iodo-3,4-methylenedioxybenzene with pinacolborane at 30 C. in which the catalyst, PdCl2(dppf).CH2Cl2, was activated, prior to employment in the reaction, with triethylamine. The concentrations are expressed in area % (uncorrected for response factors) determined by gc analysis of aliquots of the reaction solution taken at selected reaction times Reaction Time (h) [C00029] [C00030] [C00031] [C00032] 1 1.6 0 94 4.8 2 1.7 0 89 9.7 3 2 0 84 13.8 4 2 0 81 17 7 2.3 0 71 26 28 4 0.6 27 68 71.5 4.2 1.9 0 94 *Used 25 mg of PdCl2(dppf).CH2Cl2, 4 ml dioxane, 0.43 ml (3.0 mmol) triethylamine and warmed to 80 C. for 16 h. Then added 0.23 ml (1.5 mmol) pinacolborane and 262 mg (1.05 mmol) 1-iodo-3,4-methylenedioxybenzene at room temp. before warming the reaction to 80 C. The reaction was quenched at the selected reaction time by addition of the aliquot of reaction solution to a water/ethyl acetate mixture. [00219] When the catalyst PdCl2(dppf).CH2Cl2 is treated with the amine together with the borane ester prior to use in the reaction, the initial reaction rate is enhanced, indicating that some catalyst has been activated. The overall reaction, however, is slower than that when the catalyst receives no pretreatment. Catalyst presumably unactivated by the pretreatment with triethylamine and pinacolborane appears to be more resistant to activation during the progress of the boronation reaction. This can be seen by comparison of Tables 17.3 and 17.4. In Table 17.3, the catalyst was not activated prior to use and the reaction rate over the first 1 to 2 hours is slow. In T…

According to the analysis of related databases, 5876-51-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Commonwealth Scientific and Industrial Research Organisation; US6680401; (2004); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 40400-15-5, name is 2-(2-Iodophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Iodophenyl)acetonitrile

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 ¡Á 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3aa; yield: 32.9 mg (86%); tan yellowsolid; mp 155.6-156.3 C.

The synthetic route of 40400-15-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 696-41-3, name is 3-Iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 3-Iodobenzaldehyde

General procedure: Triton B (40% in MeOH, 7.30 mL, 17.5 mmol) was added dropwise to a solution of ethyl 2-[bis(2-isopropylphenoxy) phosphoryl]acetate (5.30 g, 13.1 mmol) in THF (150 mL) at -78 C under Ar. After 15 min of stirring, a solution of 2-methylbenzaldehyde (59) (1.50 g, 12.5 mmol) in THF (50 mL) was added dropwise to the solution. After 10 h of stirring, the mixture was quenched with satd. aq. NH4Cl (30 mL) and extracted with EtOAc (3 x 30 mL). The organic layer was washed successively with H2O, satd. aq. (20 mL) NaHCO3 (20 mL) and brine (20 mL), then dried (MgSO4), filtered and concentratedin vacuo.; Z-selective olefination of 3-iodobenzaldehyde (87) was performedusing the procedure described above to provide (Z)-ethyl3-(3-iodophenyl)acrylate (cis-143) (94%, Z:E = 98:2, determinedby 1H-NMR spectrum) (silica gel CC, EtOAc/hexane, 5:95) as acolorless oil: 1H-NMR (CDCl3, 270 MHz) d: 1.26 (t, J = 7.2 Hz, 3H,-CH3), 4.19 (q, J = 7.2 Hz, 2H, -CH2-), 5.98 (d, J = 12.6 Hz, 1H,CH-CO2-), 6.85 (d, J = 12.6 Hz, 1H, Ar-CH), 7.10 (t, J = 7.8 Hz,1H, Ar-H), 7.53, 7.66 (d, J = 7.8 Hz, each 1H, Ar-H), 7.90 (s, 1H,Ar-H).

The synthetic route of 696-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishikawa, Keisuke; Fukuda, Hiroshi; Abe, Masato; Nakanishi, Kazunari; Taniguchi, Tomoya; Nomura, Takashi; Yamaguchi, Chihiro; Hiradate, Syuntaro; Fujii, Yoshiharu; Okuda, Katsuhiro; Shindo, Mitsuru; Phytochemistry; vol. 96; (2013); p. 132 – 147;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 101066-87-9, name is 4-Iodo-2-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-Iodo-2-(trifluoromethyl)benzonitrile

To the suspension of zinc powder (without activation, 65.4 mg, 1.0 mmol, Aldrich 99.995 % purity) in DMPU (0.5 mL), trifluoromethyl iodide (ca. 2.5 mmol, sufficiently dissolved in the solution) was added at room temperature under argon atmosphere. The solution was stirred for 2 h, and CuI (9.5 mg, 0.05 mmol, 10 mol %) and 4-iodo-2-(trifluoromethyl)benzonitrile (1c, 148.5 mg, 0.5 mmol) were added. The reaction mixture was stirred at 50 C for 24 h. The reaction mixture was quenched with H2O (5 mL), and then Et2O (5 mL) was added. After filtration over celite, the organic layer was separated, and the aqueous layer was extracted with Et2O (5 mL ¡Á 3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4, and evaporated. The resulting crude product was purified by silica gel column chromatography (pentane/Et2O 9:1) to give the product 2c (83 mg, 70% yield) as a colorless liquid. 1H NMR (300 MHz, CDCl3) delta 8.06 (s, 1H), 8.03 (d, J =8.2 Hz, 1H), 7.98 (d, J = 8.2 Hz, 1H); 13C NMR (400 MHz, CDCl3) delta 135.5, 135.0 (q, JCF = 34.4 Hz), 134.0 (q, JCF = 33.5 Hz), 129.3 (q, JCF = 3.6 Hz), 124.1-123.9 (m), 122.3 (q, JCF =271.9 Hz), 121.6 (q, JCF = 272.7 Hz), 114.1, 113.9; 19F NMR (282 MHz, CDCl3) delta -62.2 (s, 3F), -63.6 (s, 3F); HRMS-ESITOF (m/z): [M – H]- calcd for C9H2F6N, 238.0091; found, 238.0086; FTIR (neat, cm-1) 2238, 1344, 1146, 1279, 1082.

The synthetic route of 101066-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nakamura, Yuzo; Fujiu, Motohiro; Murase, Tatsuya; Itoh, Yoshimitsu; Serizawa, Hiroki; Aikawa, Kohsuke; Mikami, Koichi; Beilstein Journal of Organic Chemistry; vol. 9; (2013); p. 2404 – 2409;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 54435-09-5, A common heterocyclic compound, 54435-09-5, name is 2-Iodo-4-methoxybenzoic acid, molecular formula is C8H7IO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(c) A mixture of 2-iodo-4-methoxybenzoic acid (13.6 g, 48.9 mmol), 5-amino-1-ethylpyrazole (5.5 g, 49 mmol), DMF (100 ml), K2 CO3 (6.9 g, 0.05 mol) and Cu(OAc)2 (0.5 g) was refluxed overnight. The reaction mixture was poured into water (500 ml) and acidified with acetic acid to a pH of 5-6. The product slowly crystallized from the solution and was collected by filtration and washed with water. The solid was taken up in CH2 Cl2 /methanol, dried, filtered and evaporated. The residue was combined with POCl3 (60 ml) and refluxed overnight. The reaction mixture was cooled, poured into water and neutralized with concentrated NH4 OH. The mixture was extracted with CH2 Cl2, and the CH2 Cl2 extracts were evaporated and the residue was purified by column chromatography on silica gel eluding with ethyl acetate to afford 5 g of 1-ethyl-4-chloro-7-methoxy-1H-pyrazolo[3,4-b]quinoline, m.p. 114-115 C.

The synthetic route of 54435-09-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sanofi Winthrop Inc.; US5488055; (1996); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 90347-66-3, name is Methyl 3-iodo-4-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 3-iodo-4-methylbenzoate

Compound 27.1. Methyl 3-acetyl-4-methylbenzoate. Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 4.50 g, 16.3 mmol), 1- (vinyloxy)butane (4.21 mL, 32.6 mmol), TEA (4.53 mL, 32.5 mmol), 1,3- bis(diphenylphosphino)propane (672 mg, 1.63 mmol) and Pd(OAc)2 (349 mg, 1.55 mmol) in DMSO (50 mL). The mixture was stirred for 12 hours at 120 C, then cooled to room temperature. The pH was adjusted to 1-2 with aqueous hydrogen chloride (2 M) and stirred for 1 hour. The aqueous phase was extracted with ethyl acetate (3 x 200 mL) and the combined organic layers were washed with water (100 mL), then brine (3 x 100 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1 :50) as the eluent to yield 1.45 g (46%) of the title compound as a yellow solid.

According to the analysis of related databases, 90347-66-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; 3-V BIOSCIENCES, INC.; HEUER, Timothy Sean; OSLOB, Johan D.; MCDOWELL, Robert S.; JOHNSON, Russell; YANG, Hanbiao; EVANCHIK, Marc; ZAHARIA, Cristiana A.; CAI, Haiying; HU, Lily W.; WO2015/95767; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 1258298-01-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1258298-01-9 name is 2,6-Dichloro-4-iodobenzoic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: A mixture of 2-chloropyridine-3,4-diamine(2.80 g, 19.4mmol), 2,6-dichlorobenzoic acid(3.71 g, 19.4mmol)andpolyphosphoricacid (50 g) was heated at 190 Cfor 3 h with stirring. The mixture was cooled to room temperature and poured into ice/water. The resulting mixture was neutralized by addition of aq. saturated Na2CO3solution. The crude product was collected by filtration, washed with water, and dried to afford a brown solid(5.4 g, 97% yield).1H NMR(DMSO-d6, 500 MHz):delta13.08 (s, 1H), 11.21 (s, 1H), 7.67-7.58 (m, 3H),7.15 (m, 1H), 6.49 (d,J= 7.0 Hz, 1H).LCMS(ESI) m/z: 280.0 [M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dichloro-4-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Article; Liang, Jun; Van Abbema, Anne; Balazs, Mercedesz; Barrett, Kathy; Berezhkovsky, Leo; Blair, Wade S.; Chang, Christine; Delarosa, Donnie; DeVoss, Jason; Driscoll, Jim; Eigenbrot, Charles; Goodacre, Simon; Ghilardi, Nico; MacLeod, Calum; Johnson, Adam; Bir Kohli, Pawan; Lai, Yingjie; Lin, Zhonghua; Mantik, Priscilla; Menghrajani, Kapil; Nguyen, Hieu; Peng, Ivan; Sambrone, Amy; Shia, Steven; Smith, Jan; Sohn, Sue; Tsui, Vickie; Ultsch, Mark; Williams, Karen; Wu, Lawren C.; Yang, Wenqian; Zhang, Birong; Magnuson, Steven; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4370 – 4376;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com