Month: June 2021

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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., Formula: C2H2IN

A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 118a (6.70 g, 37.4 mmol), Iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture in 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfateheptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C to 35 C, until the color of the reaction mixture is deep red. If TLC show the reaction not completed, then more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalent) were added in the same manner until the reaction is completed. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with saturated Sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 118b as a yellow oil: ]H NMR (500 MHz, CDC13) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J = 6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J = 6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

The synthetic route of 624-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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. 620621-48-9, name is Methyl 2-chloro-5-iodobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 620621-48-9

Intermediate 71 : methyl 2-chloro-5-(4-(dimethylamino)piperidin-l-yl)benzoate; Methyl 2-chloro-5-iodobenzoate (1.0Og, 3.37 mmol), cesium carbonate (0.360 mL,4.50 mmol), BINAP (0.070 g, 0.11 mmol), palladium(II) acetate (0.025 g, 0.11 mmol) and 4-(dimethylamino)piperidine (0.519 g, 4.05 mmol) were suspended in dioxane (18 mL) and sealed into a microwave tube. The reaction was heated to 120 0C for 3 hours in the microwave reactor and cooled to RT. The reaction mixture was filtered through celite. The crude product was purified by flash silica chromatography, elution gradient 0 to 10%NHVMeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 2-chloro- 5-(4-(dimethylamino)piperidin-l-yl)benzoate (0.456 g, 68.3 %) as a yellow oil. m/z (ESI+) (M+H)+ =297.45; HPLC tR = 1.01 min. 1H NMR (400.13 MHz, CDC13) delta 1.56 – 1.66 (2H, m), 1.93 (2H, d), 2.24 – 2.29 (IH, m), 2.31 (6H, s), 2.71 – 2.78 (2H, m), 3.71 (2H, d), 3.92 (3H, s), 6.94 – 6.97 (IH, m), 7.27 – 7.28 (IH, m), 7.33 (IH, d).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AstraZeneca AB; AstraZeneca UK Limited; WO2009/47558; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, 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 5471-81-8, category: iodides-buliding-blocks

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10mol%),Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),Glycidyl butyrate (0.6 mmol, 3.0 equiv.)And dry N-methylpyrrolidone (1.0 mL).The reaction flask was capped and stirred at room temperature for about 5 minutes.The mixture was then heated to 80 C and stirred for 24 hours. After the reaction mixture was cooled to EtOAc EtOAc EtOAc m. Purified by column chromatography, the eluent was petroleum ether: ethyl acetate = 10:1 (v/v),53 mg of methyl 7-methyl-2-(butyryloxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (light yellow oily liquid, yield 91%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-iodo-3-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 32024-15-0, These common heterocyclic compound, 32024-15-0, name is 3-Iodo-4,5-dimethoxybenzaldehyde, 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.

General procedure: Synthesis of iodo-chrysin derivatives was accomplishedfollowing the general methods shown in Schemes 1 and 2.As outlined in Schemes 1 and 2, under anhydrous andanaerobic conditions, ZnCl2 (0.05 mol) was added to themixture of resorcinol (0.1 mol) and chloroacetonitrile (0.12mol) in diethyl ether (50 mL) cooled to 0C. The mixturewas reacted with anhydrous hydrogen chloride gas for 12hours. Intermediate compound 1, chrysin derivatives 2-5were synthesized according to Scheme 2. The Baker-VenKataraman reaction was employed in the synthesis ofchrysin derivatives [31]. 2, 4-dihydroxybenzoyl chloride (86mmol) was obtained after recrystallization with water. 2-Iodobenzaldehyde, 3-iodobenzaldehyde, 2-fluorine-5-iodobenzaldehyde or 3-iodo-4,5-dimethoxy benzaldehyde(12 mmol) and 10% NaOH (20 mL) were added to a solutionof compound 1 (10 mmol) in alcohol (5 mL). The mixturewas stirred at room temperature for 72 hours. Then the solutionwas acidified with 10% aqueous HCl to pH= 7 andstirred for another 48 hours at room temperature. The crudeproduce was purified by column chromatography (ethylacetate/ petroleum ether = 1:1) to get products, compound2: 7-hydroxy-2-(2-iodophenyl)-4H-chromen-4-one yielded62.7%, compound 3: 7-hydroxy-2-(3-iodophenyl)-4Hchromen-4-one yielded 61.5%, compound 4: 2- (2-fluoro-5-iodo- phenyl)-7-hydroxy-4H-chromen-4-one yielded 60.8%,compound 5:7-hydroxy-2-(3- iodo-4,5-di- methoxyphenyl)-4H-chromen-4-one yielded 62.3%. All compounds were yellowproducts.

The synthetic route of 32024-15-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Yun; Zheng, Qutong; Tang, Guotao; Song, Chen; Wang, Guan; Zhang, Yinxiang; Xiao, Yan; Zeng, Xianliang; Wang, Zongbao; Xiao, Jichang; Zheng, Xing; Medicinal Chemistry; vol. 12; 5; (2016); p. 441 – 447;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 7681-82-5, These common heterocyclic compound, 7681-82-5, name is Sodium iodide, 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.

Synthesis of 49; A Schlenk tube was charged with complex 3 (83.4 mg, 0.18 mmol), Nal (539.6 mg,3.6 mmol), and 5 mL of THF. The reaction mixture was stirred at room temperature for 8 h. All volatiles were removed under vacuum. The residue was dissolved in toluene, and the resulting suspension was passed through a plug of Celite. All the volatiles were removed, and the residue was washed with diethyl ether (3 x 5 mL) to give 49 as a dark red powder. Yield: 68% (78.5 mg, 0.12 mmol).1H NMR (CD2C12, 300 MHz): delta 7.19 (s, 2H,CHiinid), 5.69 (d, J = 5.91 Hz, 2H, CHpCym), 5.52 (septet, J = 6.60 Hz, 2H, CHiSoP imid), 5.15 (d, J = 5.88 Hz, 2H, CHpcym), 3.29 (septet, J = 6.93 Hz, 1H, CHjsop pcym ), 2.01 (s, 3H, CH3pcym), 1.44 (br, 12H, CH3isop imid), 1.32 (d,13C {1H} NMR (CD2C12, 100MHz): delta 167.6 (C-Ru), 120.1 (CHimid), 108.4 (Cqpcym), 99.8( qpcym), 87.3 (CHpcym), 82.3 (CHpcym), 55.0 (CHjsop jmid), 32.0 (CHjSop pcym), 25.7 (CH3jsop imid), 25.1 (CH3jsop imid), 23.2 (CH3isop pcym), 19.8 (CH3pcym).Anal, calcd for C20H32C12I2N2-Ru (49-3CH2Cl2, 726.3): C, 33.08; H, 4.44; N, 3.86. Found: C, 33.46; H, 4.01; N, 4.03.

The synthetic route of 7681-82-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NANYANG TECHNOLOGICAL UNIVERSITY; HONG, Soon Hyeok; GHOSH, Subhash Chandra; ZHANG, Yao; MUTHAIAH, Senthilkumar; CHEN, Cheng; XU, Xiangya; WO2011/34506; (2011); A1;,
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. 351003-36-6, name is 2-Fluoro-5-iodobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3FIN

Add bis (triphenylphosphine) palladium (II) dichloride (77 mg, 0. 11 mmol), copper (I) iodide (42 mg, 0. 22 mmol), and 3-chloro-5-ethynylpyridine, (prepared as described in PREPARATION 27), (300 mg, 2. 2 mmol) to a solution of 2-fluoro-5-iodobenzonitrile (650 mg, 2. 6 mmol) in triethylamine (4. 6 mL, 33 mmol) and heat at 60 C for 6 h. Cool to room temperature and concentrate. Purify by silica gel chromatography, eluting with 50 : 50 dichloromethane : hexanes to 90 : 10 dichloromethane : ethyl acetate, followed by a second silica gel chromatography eluting with 95 : 5 to 75 : 25 hexanes : ethyl acetate, to give the title compound as an off-white solid (510 mg, 91%). 1H NMR (300 MHz, CH30H-d4) 8 7. 40-7. 48 (t, J = 8. 9 Hz, 1H), 7. 88-7. 97 (m, 1H), 8. 00-8. 09 (m, 2H), 8. 55-8. 58 (d, J = 2. 3 Hz, 1H), 8. 63-8. 66 (d, J = 1. 7 Hz, 1H) ; MS (APCI) : nz/z = 257 [M+H] +.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/94822; (2005); A1;,
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. 104539-21-1, name is 1-Iodo-2-(2-methoxyethoxy)ethane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Iodo-2-(2-methoxyethoxy)ethane

Naphthalene-2,7-diol (1) (3.0 g, 19 mmol) was added to compound 2 (4.83 g, 21 mmol) in 30 mL of acetone with K2CO3 (3 g, 21 mmol). The reaction was stirred for 24 h, and the reaction mixture was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated, and purified by silica gel column chromatography (20% ethyl acetate in hexane) to afford compound 3 as a white solid, yield (4.0 g, 82%). 1H NMR (600 MHz, CDCl3): delta 7.65-7.59 (m, 2H), 7.01-6.90 (m, 4H), 5.46 (s, 1H), 4.19 (t, J = 4.83 Hz, 2H), 3.90 (t, J = 4.83 Hz, 2H), 3.79-0.374 (m, 2H), 3.64-3.60 (m, 2H), 3.42 (s, 3H) ppm; 13C NMR (150 MHz, CDCl3): delta 157.23, 154.36, 135.86, 129.30, 129.13, 124.17, 116.19, 115.56, 108.82, 105.48, 71.95, 70.63, 69.74, 67.12, 59.03 ppm; MS (ESI): 263 [M+H]+.

The synthetic route of 104539-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeong, Jaemyeng; Kumar, Rangaraju Satish; Mergu, Naveen; Son, Young-A.; Journal of Molecular Structure; vol. 1147; (2017); p. 469 – 479;,
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. 1878-94-0, name is 2-(4-Iodophenoxy)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-(4-Iodophenoxy)acetic acid

The mixture of camptothecin (30 mg, 0.086 mmol), 4-iodophenoxyacetic acid (36 mg, 0.18 mmol), EDCI (60 mg, 0.31 mmol), DMAP (5 mg, 0.047 mmol) and dichloromethane (5 ml) was stirred in the room temperature for 20 h, then dichloromethane (20 ml) was added to the solution. Organic layer was washed with water (20 ml), saturated NaHCO3 aqueous solution (10 ml) and brine (20 ml), and then dried over MgSO4. After the solvent was removed under reduced pressure, the resulting solid was separated by column chromatography (eluent: CHCl3:CH3OH 9:1) to afford 46 mg camptothecin-20-O-4-fluorophenoxyacetate, yield: 88.0%, mp 228-230 C. The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz): delta 8.41 (s, 1H, Ar-H), 8.29 (d, 1H, Ar-H), 7.98 (d, 1H, Ar-H), 7.88 (t, 1H, Ar-H), 7.70 (t, 1H, Ar-H), 7.56 (s, 2H, Ar-H), 7.22 (s, 1H, Ar-H), 6.71 (m, 2H, Ar-H), 5.68 (d, 1H, H17), 5.40 (d, 1H, H17), 5.29 (s, 2H, H5), 4.82 (q, 2H, OCH2CO), 2.25 (d, 2H, CH2), 0.97 (t, 3H, CH3).

According to the analysis of related databases, 1878-94-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; California Pacific Medical Center; US6350756; (2002); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 7681-82-5 as follows. Recommanded Product: Sodium iodide

General procedure: Complexes 2 and 3 were synthesised by following a similar procedure as described for complex 1 but using anhydrous Cd(ClO4)2 (0.311g, 1mmol) and NaBr (0.101g, 1mmol) (For complex 2)/NaI (0.149g, 1mmol) (For complex 3) respectively instead of CdCl2 (0.183g, 1mmol). The needle shaped brown colored crystals of 2 and 3 were washed with a methanol-water mixture and dried in desiccator containing anhydrous CaCl2 and then characterized by elemental analysis, spectroscopic methods, and X-ray diffraction. Complex 2: Yield: 0.851g, 73.36% (with respect to CuL). Anal. Calc. for C50H40CdCu2Br2N4O4: C, 51.76; H, 3.48; N, 4.83. Found: C, 51.59; H, 3.41; N, 4.94%. IR (KBr pellet, cm-1): nu(C=N) 1603. UV/Vis: lambdamax(nm) [epsilonmax(M-1 cm-1)] in (DMF)=588(470), 383(29570), 313(62182). Complex 3: Yield: 0.910g, 72.56% (with respect to CuL). Anal. Calc. for C50H40CdCu2I2N4O4: C, 47.88; H, 3.21; N, 4.47. Found: C, 47.73; H, 3.07; N, 4.30%. IR (KBr pellet, cm-1): nu(C=N) 1602. UV/Vis: lambdamax(nm) [epsilonmax(M-1 cm-1)] in (DMF)=589(479), 382(38868), 313(81774).

According to the analysis of related databases, 7681-82-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ganguly, Sayantan; Bauza, Antonio; Frontera, Antonio; Ghosh, Ashutosh; Inorganica Chimica Acta; vol. 492; (2019); p. 142 – 149;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 5460-32-2, 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. 5460-32-2 name is 4-Iodo-1,2-dimethoxybenzene, 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.

4-Iodoveratrole (26.0 g, 0.0985M) in acetic acid (25 ml) was treated with bromine (6.5 ml, 0.127M) in acetic acid (30 ml) and stirred at room temperature for one hour. The mixture was diluted with water (300 ml) and treated with sodium bisulfite to discharge the excess bromine. The white solid was filtered, washed with water and dried in vacuo over P2 O5 to give 4-bromo-5-iodoveratrole (33.0 g, 95percent yield) as a white solid, mp 98°-100° C. (literature: Baker et al., J. Chem. Soc. 3986 (1961), mp 102°-104° C.). NMR (CDCl3) delta 3.83 ppm (s, 6H, (2x) OCH3), 7.06 (s, 1H, ArH), 7.21 (s, 1H, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Iodo-1,2-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Ortho Pharmaceutical Corporation; US4761413; (1988); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com