Month: June 2021

Electric Literature of 645-00-1, A common heterocyclic compound, 645-00-1, name is 1-Iodo-3-nitrobenzene, molecular formula is C6H4INO2, 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.

To a mixture of 3-iodonitrobenzene (7 g, 28.1 mmoles), K2CO3 (11.63 g, 84.3 mmoles) in 80 mL 1,2-DME/water (1: 1) were added successively CuI (229.50 mg, 1.21 mmoles), PPH3 (591.20 mg, 2.25 mmoles), Pd/C 10% (598. 0 mg, 0.562 mmoles). The mixture was stirred at room temperature for 1 hour. 4-BUTYN-1-OL (5.90 g, 84.30 mmoles) was added, then the mixture was heated to reflux overnight. After cooling, the mixture was filtered on Celite and the organic layer was evaporated under reduced pressure. Tha aqueous layer was acidified with concentrated Chlorhydric acid and extracted with AcOEt. The organic layer were washed with brine, dried, filtered and evaporated. Purified by flash CHNNATOGRAPHY on silica gel AcOEt/Hexanes (35: 65). Yield: 81% H NMR (CDC13,300 MHz) 8 : 8.29 (s, Ar, 1H), 8.17 (M, Ar, 1H), 7.74 (d, Ar, 1H, J = 8HZ), 7.51 (t, Ar, 1H, J = 8Hz), 4.53 (d, 2H, J = 6Hz). A mixture of 3-(3-nitrophenyl)-prop-2-yn-1-ol (100 mg, 0.564 mmoles), Pd/C 10% (10 mg, 0.094 mmoles) was hydrogenated under 38 psi overnight. The mixture was filtered on Celite and the filtrate was evaporated to dryness. Purified by flash chrmatography on silica gel AcOEt/Hexanes (25: 75). Yield: 99% H NMR (CDC13, 300 MHz) 8 : 7.08 (t, Ar, 1H, J = 8. 0Hz), 6.61 (d, Ar, 1H, J = 7. 5HZ), 6.53 (M, Ar, 2H), 3.67 (t, 2H, J = 6. 5HZ), 2.84 (s, 3H), 2.62 (t, 2H, J = 8. 0Hz), 1.87 (M, 2H). 3-(3-aminophenyl)propan-1-ol was then reacted with 2-chloroethylisocyanate as described in examples 1-12 to obtain desired product. Purified by flash chromatography on silica gel ETOH/CH2CL2 (2: 98).EXAMPLE 45: Preparation of Acetic acid 3- {3- [3- (2-CHLORO-ETHYL)-UREIDO]-PHENYL}-PROPYL ester (42) To a mixture OF 3-IODONITROBENZENE (1 g, 4.56 mmoles), K2CO3 (1.57 g, 11.4 mmoles) in 30 mL 1.2-DME/water (1: 1) were added successively CuI (34.78 mg, 0. 18 mmoles), PPH3 (95.80 mg, 0.36 mmoles), Pd/C 10% (97.05 mg, 0.09 mmoles). The mixture was stirred at room temperature for 1 hour. Propargyl alcohol (807 mg, 14.40 mmoles) was added, then the mixture was heated to reflux overnight. After cooling, the mixture was filtered on Celite and the organic layer was evaporated under reduced pressure. Tha aqueous layer was acidified with concentrated Chlorhydric acid and extracted with AcOEt. The combined organic layers were washed with brine, dried, filtered and evaporated. Purified by flash chromatography on silica gel CH2CL2/ETOH (95: 5). Yield: 81% IH NMR (CDC13, 300 MHz) 8 : 8.29 (s, Ar, 1H), 8.17 (M, Ar, 1H), 7.74 (d, Ar, 1H, J = 8HZ), 7.51 (t, Ar, 1H, J = 8Hz), 4.53 (d, 2H, J = 6Hz). To an ice-cold 3- (3-NITROPHENYL)-PROP-2-YN-L-OL (150 mg, 0.85 mmoles) in diethylether (10 mL) were added acetic anhydride (254.23 mg, 2.54 mmoles), triethylamine (256.54 mg, 2.54 mmoles), 4-pyrrolidinopyridine (2.52 mg, 0.017 mmoles) and the mixture was stirred at room temperature for 12 hours. The reaction was quenched by saturated solution OF NA2C03 and the mixture was extracted with AcOEt. The extracts were washed with brine, dried and evaporated. Purified by flash chromatography on silica gel AcOEt/Hexanes (8 : 2). Yield: 99% IH NMR (CDC13, 300 MHz) 8 : 8.24 (s, Ar, 1H), 8.14 (d, Ar, 1H, J = 8. 5HZ), 7.71 (d, Ar, 1H, J = 7. 5HZ), 7. 48 (t, Ar, 1H, J= 8HZ), 4. 88 (s, 2H), 2.12 (s, 3H). A mixture of acetic acid 3- (3-NITROPHENYL)-PROP-2-YNYL ester (100 mg, 0.48 mmoles), Pd/C 10% (10 mg, 0.094 mmoles) in 30 mL of dry ethanol was hydrogenated under 38 psi overnight. The mixture was filtered on Celite and the filtrate was evaporated to dryness. Purified by flash chromatography on silica gel AcOEt/Hexanes (25: 75). Yield: 81% IH NMR (CDC13,300 MHz) 8 : 7.08 (m, Ar, 1H), 6.59 (d, Ar, 1H, J = 7. 5HZ), 6.53 (m, Ar, 2H), 4.09 (t, 2H, J = 6. 5HZ), 3.66 (s, 2H), 2.60 (t, 2H, J = 8HZ), 2.06 (s, 3H), 1.93 (M, 2H). Acetic acid 3- (3-AMINOPHENYL)-PROP-2-YNYL ester was then reacted with 2-chloroethylisocyanate as described in examples 1-12 to obtain desired product. Purified by flash chromatography on silica gel ACOET/CH2CL2 (2: 8). Yield: 93%

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; IMOTEP INC.; WO2004/106291; (2004); 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. 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, A new synthetic method of this compound is introduced below., name: 4-Iodo-1,2-dimethylbenzene

General procedure: In an oven dried round bottomed flask a mixture of phenyl boronic acid (0.244g, 2.0mmol), aryl halide (2.0mmol), the palladium complex [Pd(OL1)]4 (0.002mmol) and potassium carbonate (0.145g, 2.5mmol) in THF (10cm3) was heated to reflux for 2h, as mentioned in Table 2. After the reaction was completed, the solvent was evaporated and the reaction mixture was extracted with diethyl ether. The ether solution was dried over Na2SO4 and filtered. The ether solution, containing the reaction mixture, was passed through a 30.48cm silica column (60-120 mesh), the complex was not separated out and it remained trapped in the column. After the desired compound was extracted from the column, the complex was extracted using dichloromethane. The unchanged complex was used twice. After evaporation of the ether, solids of the pure products were obtained. The yields of the products obtained from all the reactions were determined after isolation, and the products were characterized by 1H NMR spectra.

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:
Article; Pattanayak, Poulami; Pratihar, Jahar Lal; Patra, Debprasad; Lin, Chia-Her; Chattopadhyay, Surajit; Polyhedron; vol. 63; (2013); p. 133 – 138;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 111771-08-5, name is 2-Fluoro-6-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 111771-08-5, Quality Control of 2-Fluoro-6-iodobenzoic acid

Intermediate 21: 2-Fluoro-6-(2H-l,2,3-triazol-2-yl)benzoic acid To a solution of 2H-l,2,3-triazole (5.0 g, 72.46 mmol ) in DMF (20 ml) was added cesium carbonate (23.55 g, 72.46 mmol), N,N-dimethylethylenediamine (1.02 g, 7.24 mmol), copper(I) iodide (0.34 g, 1.811 mmol) and 2-fluoro-6-iodobenzoic acid (9.63 g, 36.23 mmol ) at 0-10 C. The reaction was stirred at 125C for 15 min in the microwave and then poured into water (100 ml) and extracted with ethyl acetate (100 ml x 3). The aqueous layer was acidified with dilute HC1 to pH 2 and extracted with ethyl acetate (100 ml x 3). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated in vacuo. This was then purified by column chromatography (0-3% methanol / dichloromethane) to afford the title compound.1H NMR (400 MHz DMSO- d6): delta ppm 7.43-7.47 (m, 1H), 7.66-7.72 (m, 1H), 7.78-7.80 (m, 1H), 8.13 (s, 2H), 13.71 (s, 1H)MS ES+: 208

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; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 97456-81-0, The chemical industry reduces the impact on the environment during synthesis 97456-81-0, name is 1-Bromo-3-iodo-2-methylbenzene, I believe this compound will play a more active role in future production and life.

A solution of n-Bu3MgLi (6.6 mL of 0.66 M, 4.35 mmol) in hexane-heptane- dibutylether (8:20:3) is added to l-bromo-3-iodo-2-methyl-benzene (3.69 g, 12.42 mmol) in toluene (6.0 mL) and dibutylether (3.6 mL) at 0 C and stirred at the same temperature for 3.5 h. A solution of ZnBr2-LiBr in dibutyl ether (6.51 mL of 1.05 M, 6.83 mmol) is added dropwise, cooling bath removed and stirred at RT for 1 h. A solution of [(2R,3R,4S,5S,6R)-6- bromo-3,4,5-tris(2,2-dimethylpropanoyloxy)tetrahydropyran-2-yl]methyl 2,2- dimethylpropanoate (6 g, 10.35 mmol, Ref. Sebastien Lemaire et. al. Org. Letts . 2012 , 14 , 1480-1483) in toluene (10.8 mL) is added, it is placed on pre-heated oil bath at 90 C and stirred for 24 h. The reaction mixture is cooled to RT and poured into aq. IN HC1 solution (80 mL), extracted with ethyl acetate (3 x 50 mL), combined extracts are washed with brine, dried (Na2S04) and concentrated. The residue is purified on Biotage SNAP 300 g silica gel cartridge using isocratic ethyl acetate in hexanes (10%, 4 CV) as eluent to afford title compound (4.5 g, 64.9%) as light yellow solid . 1H NMR (400 MHz, CDC13) delta 7.55 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 7.7 Hz, 1H), 7.11 (t, J = 7.9 Hz, 1H), 5.71 – 5.65 (m, 1H), 5.43 (dd, J = 6.9, 2.8 Hz, 1H), 5.30 – 5.23 (m, 1H), 5.20 (d, J = 6.0 Hz, 1H), 4.68 – 4.58 (m, 1H), 4.07 (dd, J = 12.0, 3.1 Hz, 1H), 3.87 – 3.79 (m, 1H), 2.53 (s, 3H), 1.25 (s, 9H), 1.22 (s, 9H), 1.18 (s, 9H), 1.10 (s, 9H).

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-Bromo-3-iodo-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BENNANI, Youssef, Laafiret; CADILHAC, Caroline; DAS, Sanjoy, Kumar; DIETRICH, Evelyne; GALLANT, Michel; LIU, Bingcan; PEREIRA, Oswy, Z.; RAMTOHUL, Yeeman, K.; REDDY, T., Jagadeeswar; VAILLANCOURT, Louis; YANNOPOULOS, Constantin; VALLEE, Frederic; WO2013/134415; (2013); 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. 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, A new synthetic method of this compound is introduced below., Formula: C6F13I

General procedure: In a Pyrex glass tube were placed olefin (0.2 mmol), perfluoroalkyl iodide (1.0 mmol), and CH2Cl2 (5 mL). Then Na2S2O3 (0.5 mmol, 79 mg) and water (1 mL) were added to the mixture. After sealing the tube, the mixture was shaked and then irradiated with a Hg lamp at room temperature. After the reaction was completed, the mixture was extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford pure product.

The synthetic route of 355-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yajima, Tomoko; Jahan, Ishrat; Tonoi, Takayuki; Shinmen, Manami; Nishikawa, Aya; Yamaguchi, Kanako; Sekine, Izumi; Nagano, Hajime; Tetrahedron; vol. 68; 34; (2012); p. 6856 – 6861;,
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. 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, A new synthetic method of this compound is introduced below., SDS of cas: 847685-01-2

General procedure: To a stirred mixture of aniline 2b (0.100 g, 0.344 mmol), hex-1-yne 3g (0.084 g, 1.031 mmol) and Et3N (3 mL) under argon added were Pd(PPh3)2Cl2 (0.010 g, 0.014 mmol), CuI (0.006 g, 0.031 mmol) and, additionally, Et3N (3 mL). Stirring was continued at 70 C for 3 h, the mixture was cooled to r.t., diluted by CHCl3 (10 mL) and poured into a mixture of H2O (30 mL) and CHCl3 (20 mL). The aqueous layer was extracted with CHCl3 (2 × 30 mL), the collected organic solution was washed with H2O (3 × 30 mL) and dried (MgSO4). Evoparation of the solvent and chromatography (TLC) of the crude product (eluent: hexane-EtOAc, 10:1 ? 10:1 ? 10:1, Rf = 0.54) gave aniline 4bg (0.067 g, 80%) as an oil.

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:
Article; Politanskaya, Larisa V.; Chuikov, Igor P.; Kolodina, Ekaterina A.; Shvartsberg, Mark S.; Shteingarts, Vitalij D.; Journal of Fluorine Chemistry; vol. 135; (2012); p. 97 – 107;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 42860-04-8,Some common heterocyclic compound, 42860-04-8, name is 4-Chloro-3-iodobenzoic acid, molecular formula is C7H4ClIO2, 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.

EXAMPLE 3B 4-chloro-3-iodo-N-methoxy-N-methylbenzamide A mixture of Example 3A (2.82 g, 10 mmol), EDC (2.11 g, 11 mmol), HOBt (1.68 g, 11 mmol), and N,O-dimethylhydroxylamine hydrochloride (1.26 g, 13 mmol) in DMF (30 mL) was stirred until all of the reagents dissolved, treated with triethylamine (2.54 mL, 18 mmol), stirred for 3 days at room temperature, treated with 1:1/ethyl acetate:water, stirred for 1 hour, poured into water, and extracted with ethyl acetate. The extract was washed sequentially with 2M Na2CO3, water, and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 3:1/hexanes:ethyl acetate to provide the desired product. MS (DCI/NH3) m/z 343 (M+NH4)+; 1H NMR (300 MHz, CDCl3) delta 8.2 (d, 1H), 7.65 (dd, 1H), 7.5 (s, 1H), 3.55 (s, 3H), 3.35 (s, 3H).

The synthetic route of 42860-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wang, Wei-Bo; Curtin, Michael L.; Fakhoury, Stephen A.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Hutchins, Charles W.; Li, Qun; Lin, Nan-Horng; Nelson, Lissa Taka Jennings; O’Connor, Steve; Sham, Hing L.; Sullivan, Gerard M.; Wang, Gary T.; Wang, Xilu; US2002/19527; (2002); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 401-81-0, name is 1-Iodo-3-(trifluoromethyl)benzene, 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 401-81-0, Formula: C7H4F3I

General procedure: The N-nucleophile (1.47 mmol), CuI (Sigma-Aldrich, 99.999% purity, 0.147 mmol), MnF2 (Sigma-Aldrich, 98% purity, 0.441 mmol), KOH (2.94 mmol), the aryl halide (2.21 mmol), trans-1,2-diaminocyclohexane (0.294 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 60C for 24 h. After cooling to room temperature, the mixture was diluted with dichloromethane and filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of known products was confirmed by 1H and 13C NMR spectroscopic analysis.

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:
Article; Teo, Yong-Chua; Yong, Fui-Fong; Lim, Gina Shiyun; Tetrahedron Letters; vol. 52; 52; (2011); p. 7171 – 7174;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, molecular formula is C7H6BrI, 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. Product Details of 71838-16-9

Add 2,4-dimethylaniline 37 g (186 mmol, 1 eq), 2-bromo-4-methyliodobenzene 50 g (216 mmol) to a 1000 mL three-necked flask equipped with magnetic stirring at room temperature. , 1.16eq), pd2(dba)3 1.7g (18.6mmol, 1% eq), dppf 2.06g (3.7mmol, 2% eq), sodium tert-butoxide 27g (279mmol, 1.5eq), toluene 500mL, plus The nitrogen gas was replaced 3 times, stirring was started, and the oil bath was heated to reflux (oil bath temperature 120 C) for 5 hours. The TLC tracking reaction showed that the 2,4-dimethylaniline reaction was complete (PE/EA = 20:1) and the reaction was stopped.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 71838-16-9, its application will become more common.

Reference:
Patent; Gu’an Dingcai Technology Co., Ltd.; Beijing Dingcai Technology Co., Ltd.; Gao Wenzheng; Fan Hongtao; Ren Xueyan; (25 pag.)CN109206359; (2019); A;,
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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H3BrINO2

The starting material, phenylboronic acid (76.84g, 630.2mmol) was dissolved in a THF (2780ml) in a round bottom flask, 4-bromo-1-iodo-2-nitrobenzene (309.96g, 945.3mmol), Pd (PPh 3 ) 4 (36.41g, 31.5mmol), K 2 CO 3 was (261.3g, 1890.6mmol), was added water (1390ml) and stirredat 80 . When the reaction is complete, CH 2 Cl 2 and the organic layer was extracted with water, MgSO 4 to the compound produced was dried andconcentrated to a silicagel column and the product was recrystallized 122.68g (yield: 70%) was obtained.

The synthetic route of 112671-42-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Duk San Neolux Co., Ltd.; Lee, Beom Song; Moon, Song Yun; Kim, Dae – Song; Park, Jong-chol; Lee, Gyu Min; Lee, Son-hee; (95 pag.)KR2015/87787; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com