Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, 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 5458-84-4, Recommanded Product: 5458-84-4

A mixture of 1-iodo-2-methoxy-4-nitrobenzene (1.9 g, 6.8 mmol), NaSMe (500 mg, 7.1 mmol), Pd2(dba)3 (156 mg), Xantphos (197 mg) and TEA (1.18 mL, 8.51 mmol) in THF (20 mL) was purged with argon and heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column (petroleum ether/ethyl acetate, 2:1, v/v) to give (2-methoxy-4- nitrophenyl)(methyl)sulfane as a yellow solid (400 mg, 30%).?H NMR (400 MHz, CDC13): 7.89 (dd, J = 8.8 Hz, 2.4 Hz, 1H), 7.66 (d, J = 2.4 Hz, 1H), 7.15 (d, J= 8.8 Hz, 1H), 4.00 (s, 3H), 2.51 (s, 3H).

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, 1-Iodo-2-methoxy-4-nitrobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 455-13-0, name is 4-Iodobenzotrifluoride, 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. COA of Formula: C7H4F3I

General procedure: Et3N (10 mL) and THF (10 mL) were added to 4-methoxyiodobenzene19c (1.05 g, 4.5 mmol), CuI (87 mg, 450 mmol), (Ph3P)2PdCl2(158 mg, 225 mmol) and Na ascorbate (89 mg, 450 mmol) under Ar. The mixturewas stirred at 40C for 30 min. Me3SiCCH (1.03 g, 10.5 mmol) was added and the mixture was stirred at 40C for16 h. The evaporation residue, in CH2Cl2, was washed (water,2 ) and dried. Chromatography(petroleum ether / EtOAc 99:1) gave 20c (909 mg, 99%) as an oil (lit.2oil).

The synthetic route of 4-Iodobenzotrifluoride has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumpan, Katerina; Nathubhai, Amit; Zhang, Chenlu; Wood, Pauline J.; Lloyd, Matthew D.; Thompson, Andrew S.; Haikarainen, Teemu; Lehtioe, Lari; Threadgill, Michael D.; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3013 – 3032;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 69113-59-3, name is 3-Iodobenzonitrile, 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 69113-59-3, HPLC of Formula: C7H4IN

3-Iodophenylamidoxime 3-Iodobenzonitrile (1145 mg, 5 mmol) and 5M hydroxylamine hydrochloride (1 mL, 5 mmol) in ethanol (5 mL) and 1Nsodium hydroxide (5 mL, 5 mmol), were heated at reflux for 2.5 hours. Standard work up followed by column chromatography afforded 920 mg (70.2%) of 3-iodophenylamidoxime.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 20555-91-3,Some common heterocyclic compound, 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, molecular formula is C6H3Cl2I, 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.

General procedure: In a 10 mL glass screw cap tube capped with a rubber septum, palladium acetate Pd(OAc)2, (5 mg, 0.023 mmol), 1,3-bis(diphenylphosphino)propane dppp, (9 mg, 0.023 mmol) were introduced under argon atmosphere. Then, 3 mL of freshly distilled toluene) were added under argon. The mixture was stirred for 10 min to allow formation of the catalyst. Then securinine 1 (100 mg, 0.46 mmol), potassium carbonate (K2CO3, 127 mg, 0.92 mmol) and the desired iodoarene (0.92 mmol) were added. The septum was replaced by a screw cap, and the mixture was stirred at 130 C, in an oil bath. After 24 h stirring, the reaction mixture was brought to room temperature and diluted with ethyl acetate (5 mL). The reaction mixture was filtered through a pad of Celite eluting with AcOEt (20 mL). The organic layer was extracted with a saturated aqueous solution of sodium hydrogen carbonate (10 mL) and brine (10 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification by flash column chromatography on silica gel (pentane-ethyl acetate) affords the desired coupling product. 4.1.2.1.12 (6S,11aR,11bS)-5-(3,4-Dichlorophenyl)-9,10,11,11a-tetrahydro-8H-6,11b-methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one (2l) Yield: 70%. Orange solid; m.p. 65-68 C; Rf 0.37 (petroleum ether-AcOEt, 70:30); [alpha]D20 – 477 (c = 0.11, CHCl3); 1H NMR (300 MHz, CDCl3): delta = 7.58 (d, J = 2.2 Hz, 1H), 7.46 (d, J = 8.4 Hz, 1H), 7.34 (dd, J = 8.4, 2.2 Hz, 1H), 6.81 (d, J = 1.3 Hz, 1H), 5.62 (s, 1H), 4.27 (d, J = 4.3 Hz, 1H), 2.90-2.84 (m, 1H), 2.63 (dd, J = 9.4, 4.3 Hz, 1H), 2.32-2.23 (m, 1H), 2.18 (dd, J = 11.2, 2.5 Hz, 1H), 1.89-1.82 (m, 2H), 1.68-1.47 (m, 4H), 1.27-1.12 (m, 1H); 13C NMR (75 MHz, CDCl3): delta = 173.5, 169.5, 147.6, 138.3, 133.5, 133.2, 130.8, 128.1, 125.4, 116.5, 105.6, 88.9, 62.9, 61.5, 48.7, 41.7, 27.3, 25.7, 24.0. MS (CI, NH3): m/z = 362 [M+ + H]; HRMS calcd for C19H17Cl2NO2H [M+ + H]: 362.07091; found: 362.07151, error = 1.7 ppm.

The synthetic route of 20555-91-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Perez, Marc; Ayad, Tahar; Maillos, Philippe; Poughon, Valerie; Fahy, Jacques; Ratovelomanana-Vidal, Virginie; European Journal of Medicinal Chemistry; vol. 109; (2016); p. 287 – 293;,
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. 13421-13-1, name is 4-Chloro-2-iodobenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Chloro-2-iodobenzoic acid

General procedure: The solution of 2-iodobenzoic acid (2 mmol) in thionyl chloride (2 mL) was refluxed for 1h. After completion of the reaction, the liquid was removed under reduced pressure. Then the residue was dissolved with anhydrous DCM (1 mL) and added dropwise to the mixture (DCM (1 mL), triethylamine (6 mmol) and amine (2.4 mmol) or ammonium acetate (3 mmol)). After the reaction was completed by monitoring in TLC, water (20 mL) was added to the mixture and the aqueous phase was extracted with DCM (20 mL × 3). The combined organic layers were washed with HCl (aq.2 M), saturated NaHCO3 (aq.) and brine, dried with anhydrous Na2SO4, filtered and concentrated. The crude was washed (petroleum ether/dichloromethane = 50/1, v/v) and filtered to afford 1b-x.

The synthetic route of 13421-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yingying; Zhou, Yang; Lei, Min; Hou, Jinjun; Jin, Qinghao; Guo, Dean; Wu, Wanying; Tetrahedron; vol. 75; 9; (2019); p. 1180 – 1185;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 25245-27-6,Some common heterocyclic compound, 25245-27-6, name is 1-Iodo-3,5-dimethoxybenzene, molecular formula is C8H9IO2, 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.

In a dry two necked flask were introduced N-[2-(1-Phenyl-cyclohexa-2,5-dienyl)-ethyl]-methanesulfonamide 3c (169 mg, 0.610 mmol), silver carbonate (336 mg, 1.22mmol), triphenylphosphine (24 mg, 0.092 mmol), 3,5-dimethoxy-iodobenzene 4b (322 mg, 1.22mmol), palladium acetate (6.8 mg, 0.030 mmol) and acetonitrile (24.5 mL). The mixture waswarmed to 85C and stirred for 16 hours. The mixture was filtered through celite, which wasthen washed with ethyl acetate. Evaporation of the solvents led to a paste, which was purifiedthrough silica gel chromatography (Petroleum ether/EtOAc 70:30), affording 5c as a white solid(98 mg, 39%). Mp = 123-125 C. IR (solid, KBr, numax, cm-1): 3295, 2936, 2255, 1606, 1454,1316, 1203, 1149, 1064, 973, 910, 777, 735, 710. 1H NMR (300 MHz, CDCl3): deltaH 1.53-1.63(1H, m, CHaHxCH2N), 1.90 (1H, d, 3JHH 6.0 Hz, CH cyclopropane), 1.93-2.00 (1H, m,CHaHxCH2N), 2.36 (1H, dta, JHH 6.0, 2.5 and 2.5 Hz, CH cyclopropane), 2.82 (3H, s,NSO2CH3), 3.00-3.10 (2H, m, CH2N), 3.19-3.23 (1H, m, CH cyclopropane), 3.78 (6H, s, OCH3 x2), 4.43 (1H, broad s, NH), 5.16 (1H, ddd, JHH 5.3, 2.2 and 1.5 Hz, CH olefinic), 5.91 (1H, dta, J= 5.3, 2.0 and 2.0 Hz, CH olefinic), 6.33 (1H, t, 4JHH 2.3 Hz, CH aromatic), 6.36 (1H, t, 4JHH 2.3Hz, CH x 2 aromatic), 7.17-7.35 (5H, m, 5CH aromatic). 13C NMR (75.5 MHz, CDCl3): 36.9(CH cyclopropane), 37.7 (C aliphatic), 37.9 (CH cyclopropane), 40.0 (NSO2CH3), (CH2N), 41.7(CH2CH2N), 51.3 (CH allylic), 55.4 (OCH3 x 2), 98.5 (CH aromatic), 105.8 (CH x 2 aromatic),126.6 (CH aromatic), 128.2 (CH x 2 aromatic), 131.6 (CH olefinic), 131.7 (CH x 2 aromatic),134.1 (CH olefinic), 137.5, 146.6 (2C aromatic), 160.9 (C x 2 aromatic). MS(SIMS) m/z (%):436 (M+Na, 35), 414 (M+H, 100), 305 (35). HRMS calcd for (M+H) C23H28NO4S 413.1661;found 413.1655 (1.5 ppm).

The synthetic route of 25245-27-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lebeuf, Raphael; Robert, Frederic; Landais, Yannick; ARKIVOC; vol. 2014; 3; (2013); p. 6 – 17;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

58755-70-7, name is 1-Iodo-4-methoxy-2-nitrobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1-Iodo-4-methoxy-2-nitrobenzene

2-Iodo-5-methoxy-N-(4-methoxybenzyl)aniline (7f): 12 Iron (1.68 g, 30.0 mmol)was added in one portion to a stirred solution of NH4Cl (2.67 g, 500 mmol) in H2O(50 mL), and the resulting suspension was stirred at rt for 5 min. A solution of 1-iodo-4-methoxy-2-nitrobenzene (2.79 g, 10.0 mmol) in EtOH (100 mL) was then added, the resulting mixture was slowly warmed up to 60 C, and stirring was continued at this temperature for 2 h. The reaction mixture was filtered through a short pad of Celite, and the filtrate was extracted with EtOAc (3 × 50 mL). The combined organic fractions were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated to give crude 2-iodo-5-methoxyaniline (2.35 g) as a brown oil, which was used in the next step without additional purification. From this material and 4-methoxybenzaldehyde (1.28 g, 9.44 mmol), compound 7f (2.89 g, 78% overtwo steps) was obtained according to GP1b as a colorless oil, which spontaneously crystallized when stored in a freeze

The synthetic route of 58755-70-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rassadin, Valentin A.; Scholz, Mirko; Klochkova, Anastasiia A.; De Meijere, Armin; Sokolov, Victor V.; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 1932 – 1939;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

82998-57-0, name is 3-Iodo-4-methylbenzoic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C8H7IO2

Reference Example 8 4-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl) benzoic acid (Compound A8) 3-Iodo-4-methyl benzoic acid (26.2 g, 100 mmol) was dissolved in DMF (300 mL), and then bis(pinacolate)diboron (38.1 g, 150 mmol), [1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (8.17 g, 10.0 mmol) and potassium acetate (49.0 g, 500 mmol) were added thereto, followed by stirring under argon atmosphere at 100C for 6 hours. To the reaction mixture was added 1 mol/L of hydrochloric acid, followed by extraction with ethyl acetate, an organic layer was washed with brine, followed by drying over anhydrous magnesium sulfate, and activated carbon (1 g) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was filtered through celite, followed by washing with ethyl acetate: The solvent was evaporated, and the resulting crystals were recrystallized from isopropyl ether, followed by filtration to obtain Compound A8 (18.5 g, 71%). 1H NMR (300 MHz, CDCl3) delta (ppm) 1.36 (s, 12H), 2.61 (s, 3H), 7.26 (d, J = 8.1 Hz, 1H), 8.02 (dd, J = 8.1, 1.8 Hz, 1H), 8.49 (d, J = 1.8 Hz, 1H).

The synthetic route of 82998-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2269993; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 19094-56-5, name is 2-Chloro-5-iodobenzoic acid, 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 19094-56-5, HPLC of Formula: C7H4ClIO2

General procedure: To a solution of the appropriate carboxylic acid (1.88 mmol) in anhydrous DMF (4 mL) were successively added, N,N’-dicyclohexylcarbodiimide (427 mg, 2.07 mmol) and 1-hydroxybenzotriazolehydrate (280 mg, 2.07 mmol) under argon. The reaction was stirred at room temperature for 30 min, and a solution of N,N-diethylethylenediamine (291 mL, 2.07 mmol) in distilled N,N-diisopropylethylamine (655 mL, 3.76 mmol) was added. The resulting mixture was stirred at room temperature for 16-21 h. After addition of water (15 mL), the solid was filtered off and washed with water (2 x 10 mL). The filtrates were pooled and extracted with ethyl acetate (4 x 40 mL). The combined organic layers were washed with a 5% aqueous sodium hydrogen carbonate solution (2 x 15 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane/ethanol, 9/1, v/v).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 627-31-6, 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. 627-31-6, name is 1,3-Diiodopropane(stabilized with Copper chip), This compound has unique chemical properties. The synthetic route is as follows.

Example 4General Procedure for the Preparation of Alkyl Ester IodidesAlkyl ester iodides were prepared via reaction between methyl 2-methylpropanoate and appropriate alkyl diodide in the presence of butylithium and diisopropylamine according to the following process: under inert atmosphere, N,N-diisopropylamine (1.1eq) was dissolved in tetrahydrofuran (10eq). To the solution cooled down to 0 C. was added n-butyllithium (1.1eq) drop by drop. The solution was then cooled to -70 C. before adding 2-methylpropanoic acid (1eq). The mixture was stirred at -70 C. for 15 minutes. The appropriate diiodated derivative (2eq) was added drop by drop at -70 C., and then the reaction mixture was gradually warmed to room temperature and stirred for 20 hours. The solution was then hydrolysed by adding HCl 2N to reach acidic pH. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was chromatographed over silica gel.Example 4.1 methyl 2,2-dimethyl-5-iodo-pentanoate Prepared following the general procedure previously described using methyl 2-methylpropanoate and 1,3-diiodopropane. The residue was chromatographed over silica gel (eluent cyclohexane). The product was obtained as a pale yellow oil. Yield: 79% Rf (cyclohexane/ethyl acetate 98/2): 0.32 NMR 1H (CDCl3): 1.20 (s, 6H); 1.62 (m, 2H); 1.78 (m, 2H); 3.15 (t, 2H, J=7 Hz); 3.69 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 1,3-Diiodopropane(stabilized with Copper chip). I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENFIT; US2010/4159; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com