Category: 71838-16-9

71838-16-9, These common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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.

[(2-Bromo-4-methyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester: A solution of (bromo-difluoro-methyl)-phosphonic acid diethyl ester (25.00 g, 93.6 mmol) in N,N-dimethylacetamide (50 mL) was added drop wise into a suspension of activated zinc (6.12 g, 93.6 mmol) under Argon. The reaction was initiated by heating and kept under 50 C. After the mixture was stirred for 3 h, copper (I) bromide (13.43 g, 93.6 mmol) was added and stirred for 1 h. A solution of 2-bromo-l-iodo-4-methyl-benzene (11.88 g, 40.0 mmol) in N,N-dimethylacetamide (25 mL) was added slowly to the reaction mixture. The resulting suspension was then stirred at room temp for 18 h. Water (100 mL) was added to the reaction mixture and the solution filtered through celite. The filtrate was diluted with EtOAc (250 mL) and organic layer was washed with H20 (50 mL), NaHC03 (5%, 50 mL) and H20 (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel, eluting with hexanes/EtOAc (4:1) to provide a colorless oil (11.75 g, 82%): .H NMR (300 MHz, CDC13) 8 7.51 (d, 1H), 7.49 (s, 1H), 7.19 (d, 1H), 4.26 (m, 4H), 2.36 (s, 3H), 1.48 (s, 9H), 1.37 (m, 6 H).

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 71838-16-9.

Reference:
Patent; CENGENT THERAPEUTICS, INC.; WO2006/28970; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 71838-16-9,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.

General procedure: Method B: To a 10 mL sealed vial was added Cu(OAc)2·H2O (20 mg, 0.1 mmol), N-methoxy-1H-pyrrole-2-carboxamide (14 mg, 0.1mmol), aryl halide (1.0 mmol), aminobenzenethiol (1.2 mmol), KOH (224 mg, 4.0 mmol), PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 15 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 40 mL) and water (40 mL). The combined organic phases were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 71838-16-9, These common heterocyclic compound, 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 activated Zn (1.2g, 19mmol) in DMA (7mL) was added bromodifluoromethyldiethyl- phosphonate (5.0g, 19mmol) in DMA (7mL). The resulting mixture was stirred at 45C for 3 hours, after which copper(I) bromide (2.7g, 19mmol) was added and stirring was continued for 0.5 hours at room temperature. 3-Bromo-4-iodotoluene (2.8g, 9.4mmol) was then added and the mixture was sonicated at room temperature for 12 hours. The reaction mixture was partitioned between ether and H2O, filtered through Celite, and the organic layer was dried over MgSO4 and concentrated in vacuo to yield 2.1 g (63%) of 27 as a clear, colorless oil;1H NMR (300 MHz, CDCl3) delta 7.51 (d, J = 6 Hz, 1 H), 7.27 (s, 1 H), 7.20 (d, J= 7.5 Hz, 1 H), 4.27 (m, 4 H), 1.36 (t, J = 8.1 Hz)

Statistics shows that 2-Bromo-1-iodo-4-methylbenzene is playing an increasingly important role. we look forward to future research findings about 71838-16-9.

Reference:
Patent; CENGENT THERAPEUTICS, INC.; WO2006/9876; (2006); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 71838-16-9, 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. 71838-16-9 name is 2-Bromo-1-iodo-4-methylbenzene, 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.

The 170mg (1mmol) 5- chlorobenzothiazole, 534 (1.8mmol) 4- bromo-1-iodo-toluene, 12.5mg (0.05mmol) CuSO4·5H2O14mg(0.1mmol)L1690mg(5mmol)K2CO3, 2gPEG100, was added 10mL reaction tube, sealed, under the reaction condition of 80 14h.After the reaction was stopped, extraction with ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure, column chromatography was purified by silica gel column to give 2-chloro-8-methyl-phenothiazine piperazine 161mg, yield 65%.

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

Reference:
Patent; Sun Yat-sen University; Wan, Yiqian; Huang, Manna; Huang, Dongting; Zhu, Xinhai; (11 pag.)CN104529938; (2016); B;,
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

Adding a certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9, SDS of cas: 71838-16-9

General procedure: The following were charged to a screw-capculture tube: siloxane 8a (0.101 g, 0.703 mmol, 1.0 equiv), THF (4 mL), 1-iodo-2,5-dimethoxy-4-methylbenzene (9) (0.293 g, 1.05 mmol, 1.5 equiv), and TBAF (1.40 mL 1 M in THF, 1.40 mmol) followed byPd2(dba)3 (0.064 g, 0.070 mmol, 10 mol %). The tube was capped and after stirring 5 min, the tube was placedin a 50 C oil bath for 18 h. The cooled mixture was filtered through a plug of silica gel, rinsing the plug with Et2O. The filtrate was concentrated by rotary evaporation and purified by flash chromatography (2:1hexanes:EtOAc) to provide 10 as a pale yellow oil (0.152 g, 0.643 mmol, 92%).

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; Vyvyan, James R.; Engles, Courtney A.; Bray, Scott L.; Wold, Erik D.; Porter, Christopher L.; Konev, Mikhail O.; Beilstein Journal of Organic Chemistry; vol. 13; (2017); p. 2122 – 2127;,
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 71838-16-9 as follows. Application In Synthesis of 2-Bromo-1-iodo-4-methylbenzene

Step 1: Preparation of 2-(2-bromo-4-methylphenyl)-1,3-difluoropropan-2-ol To a solution of 2-bromo-1-iodo-4-methylbenzene (18.5 g, 62.3 mmol) in THF (25 mL) at 0 C. was slowly added i-PrMgCl (24 mL, 24 mmol). After being stirred for 1 h at 0 C., the reaction mixture was cooled to -78 C. Then a solution of 1,3-difluoropropan-2-one (0.85 g, 9.04 mmol) in dry THF (25 mL) was added. The mixture was stirred at -70 C. for 1 h, and then dry ice bath was removed. The solution was acidified with HCl (2 N) and extracted with EA (60 mL*2). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, eluting with PE:EA (5:1) to give 2-(2-bromo-4-methylphenyl)-1,3-difluoropropan-2-ol (1.3 g, yield 55%) as colorless oil. 1H NMR (400 MHz, DMSO-d6): delta 7.60 (d, 1H), 7.46 (s, 1H), 7.21 (d, 1H), 6.21 (s, 1H), 4.97-4.94 (m, 1H), 4.85-4.82 (m, 2H), 4.74-4.71 (m, 1H), 2.26 (s, 3H) ppm.

According to the analysis of related databases, 71838-16-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 71838-16-9,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.

General procedure: Method B: To a 10 mL sealed vial was added Cu(OAc)2·H2O (20 mg, 0.1 mmol), N-methoxy-1H-pyrrole-2-carboxamide (14 mg, 0.1mmol), aryl halide (1.0 mmol), aminobenzenethiol (1.2 mmol), KOH (224 mg, 4.0 mmol), PEG-100 (2.0 g) and a magnetic stir bar. The reaction mixture was stirred in an oil bath preheated to 90 C for 15 h. After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 × 40 mL) and water (40 mL). The combined organic phases were washed with brine, dried overanhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-iodo-4-methylbenzene, its application will become more common.

Reference:
Article; Huang, Manna; Hou, Jianying; Yang, Ruiqiao; Zhang, Liting; Zhu, Xinhai; Wan, Yiqian; Synthesis; vol. 46; 24; (2014); p. 3356 – 3364;,
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 71838-16-9 as follows. Recommanded Product: 2-Bromo-1-iodo-4-methylbenzene

Step A. 4-(2′-bromo-4′-methylbiphenyl-4-yl)-1-(2,2,2-trifluoroethyl)piperidine A mixture of 2-bromo-1-iodo-4-methylbenzene (0.764 g, 2.57 mmol), the title compound from Example 60 Step B (1.00 g, 2.71 mmol), dichloro bis(triphenylphosphine)palladium(II) (0.095 g, 0.135 mmol), sodium carbonate (5.42 mL of 1 M solution, 5.42 mmol) and MeCN (5.42 mL) was heated at 110 C. overnight. Organic layer was separated. Aqueous layer was extracted with hexanes-EtOAc. The organic layers were combined and concentrated. Silica gel flash chromatography eluting with hexanes:EtOAc (20:1 to 9:1 v/v) gave the title compound: LCMS m/z 414.0 [M+H+]; 1H NMR (500 MHz, CDCl3) delta 7.54 (s, 1H), 7.40 (d, J=8.1 Hz, 2H), 7.31 (d, J=8.1 Hz, 2H), 7.26 (d, J=7.8 Hz, 1H), 7.20 (d, J=7.8 Hz, 1H), 3.16 (m, 2H), 3.08 (q, J=9.8 Hz, 2H), 2.57 (m, 3H), 2.42 (s, 3H). 1.95-1.88 (m, 4H).

According to the analysis of related databases, 71838-16-9, the application of this compound in the production field has become more and more popular.

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. 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, A new synthetic method of this compound is introduced below., name: 2-Bromo-1-iodo-4-methylbenzene

General procedure: To a stirred solution of o-bromoiodobenzene (1.3 ml, 10 mmol) in THF (10 ml) wasadded dropwise a solution of i-propylmagnesium chloride (2.0 M in THF, 5 ml, 10mmol) at -40 C. After 1 h, PCl3 (0.9 mL, 10 mmol) was added and stirred for 40 minat the same temperature. The mixture was then allowed to stand at room temperaturefor 12 h and cooled at -40 C again. A solution of proper arylmagnesium bromide (1.0M in THF, 22 ml, 22 mmol) was added dropwise. After 1 h, the resulting mixture wasthen stirred at room temperature overnight. Saturated aqueous solution of ammoniumchloride was added and the reaction mixture was extracted with Et2O three times. Thecombined organic layer was washed with water and brine and dried over magnesiumsulfate. The solvent was then evaporated in vacuo and the residue was purified bysilica gel column chromatography with hexane as eluent to afford the correspondingphosphines. After oxidation by H2O2 in acetone, the crude products were purified byusing flash chromatography with ethyl acetate as eluent, giving the pure products.Compounds 1d, 1e, 1f, 1l has been reported in our previous work.

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; Lin, Yan; Ma, Wei-Yang; Sun, Qiao-Ying; Cui, Yu-Ming; Xu, Li-Wen; Synlett; vol. 28; 12; (2017); p. 1432 – 1436;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com