Category: 67832-11-5

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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 67832-11-5

To a solution of 4-bromo-2-methylbenzonitrile (2.0 g, 10.2 mmol) in THF (100 ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5 M solution of n-butyl lithium (4.48 ml, 11.2 mmol). The mixture was stirred at -78C for 1h and then poured onto solid carbon dioxide (5 g) in THF (50 ml). The mixture was allowed to warm to room temperature. Water was added (200 ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HCl and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgSO4, and concentrated in vacuo to give a white solid identified as 4-cyano-3-methylbenzoic acid (1.2 g, 73%).

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; Ferring B.V.; EP1449844; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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 6-bromo-l -chlorophthalazine (18) Step A: A mixture of 4-bromo-2-methylbenzonitrile (14, 22 g, 112 mraol), benzoyl peroxide (2.7 g, 11 mmol) in 400 mL carbon tetrachloride was treated with n- bromosuccimide (21 mL, 247 mmol) at RT, then warmed up to 90 0C and stirred for 15 h. After 15 h of reaction, another 20 g of NBS was added and the reaction was stirred at 90 0C for another 1O h. Thin layer chromatography (TLC) revealed that all the starting material had been consumed. The reaction was cooled down to RT, filtered, and washed with hexane (100 mL). The filtrate was concentrated in vacuo, and the crude product was purified via flash chromatography (silica gel) eluting with a gradient of 4/1 hexanes/EtOAc to 2/1 hexanes/EtOAc, to give as a white solid, 4-bromo-2- (dibromomethyl)benzonitrile IS, 29.6g. Found MS (ES+): 354 (M+H)+.

Statistics shows that 4-Bromo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 67832-11-5.

Reference:
Patent; AMGEN INC.; TASKER, Andrew; ZHANG, Dawei; WO2008/30466; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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.

Preparation 14: 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzonitrile; A mixture of dichloro[1 ,1 ,’-bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (2.12 g, 2.55 mmol), potassium acetate (7.66 g, 76.5 mmol), and bis(pinacolato) diboron (7.12 g, 28.1 mmol) was flushed with nitrogen. 1 ,2- dimethoxyethane (130 ml_) and 4-bromo-2-methylbenzonitrile (5.00 g, 25.5 mmol) were added. The reaction was stirred at 80C for 5 h. The reaction was cooled to room temperature and filtered through celite. The filtrate was diluted with ethyl acetate and washed with water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. Silica gel was added and the mixture was concentrated. The crude material was purified by silica column chromatography eluting with a gradient of 0%- 45% ethyl acetate / heptane to give the title compound (5.07 g, 82%) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta ppm 7.70 (m, 2H), 7.57 (d, 1 H), 2.45 (s, 3H), 1.26 (s, 12H).

Statistics shows that 4-Bromo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 67832-11-5.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 67832-11-5, A common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, molecular formula is C8H6BrN, 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.

A. 4-Bromo-2-methylbenzamide. A solution of 4-bromo-2- methylbenzonitrile (1.0 g, 5.1 mmol), trifluoroacetic acid (4.0 mL) and sulfuric acid (1.0 mL) were combined and heated to 65 C for 18 h. The reaction was poured into ice water and the product precipitated and was collected by filtration. The resulting material was dried under vacuum overnight to afford the title compound as a white solid (0.96 g, 88%). MS (ESI) m/z 420.5 [M+ 1]+.

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51493; (2008); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 67832-11-5, These common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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 solution of 4-bromo-2-methylbenzonitrile (4.00 g, 20.4 mmol) in THF (40 mL) was added dropwise lithium diisopropylamide (2 Mm THF, 16 mL, 32 mmol) in THF (10 mL) over a period of 20 mm at -78 C under nitrogen atmosphere. After stirring 2 hr at the sametemperature, iodomethane (3.48 g, 24.5 mmol) was added dropwise over a period of 20 mm. The mixture was warmed to room temperature, stirred for 3 h, re-cooled to 0 C and acidified with 1 N hydrochloric acid. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (0-10% ethyl acetate inpetroleum ether) to afford the title compound. LCMS [M+H] = 210.

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BISWAS, Dipshikha; DING, Fa-Xiang; DONG, Shuzhi; GU, Xin; JIANG, Jinlong; PASTERNAK, Alexander; SUZUKI, Takao; VACCA, Joseph; XU, Shouning; WO2015/103756; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 67832-11-5 as follows. Product Details of 67832-11-5

[0114] To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL), BH3 THF (45 mL, 45 mmol) was added. The solution was stirred at 0 C for 1 h and heated to 80 C for 16 h. Then the mixture was quenched with MeOH. After concentrated, the residue was stirred with saturated HCl/EtOAc solution and filtered. The filter cake was rinsed with ether (20 mL x3) and dried under vacuum to afford (4-bromo-2-methylphenyl)methanamine (3.2 g, yield: 90%) as white solid. ESI-MS (M+H)+: 200.1 Preparation of tert-butyl 4-bromo-2-methylbenzylcarbamate

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN MA INC.; MACPHEE, J. Michael; CHEN, Robbie; FERGUSON, Steven; FRANKLIN, Lloyd; MACK, Tamera, L.; (78 pag.)WO2016/201271; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 67832-11-5 as follows. HPLC of Formula: C8H6BrN

Compound BB-2H-1 (11.50 g, 58.66 mmol) was dissolved in carbon tetrachloride (150 mL) at room temperature, followed by addition of N-bromobutanimide (31.32 g, 175.98 mmol) and benzoyl peroxide (1.42 g, 5.87 mmol). After completion of the addition, the reaction mixture was heated to 85 C and stirred for 10 hours. After completion of the reaction, the mixture was cooled to room temperature, followed by filtration. The filter cake was wash with ethyl acetate (50 mL). The filtrate was combined and concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate (50 mL), washed with saturated brine (100 mL×2), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and concentrated under reduced pressure to obtain the title compound BB-2H-2 (pale-yellow solid, 20.00 g). The crude product was used directly in the next step without purification. 1H NMR (400MHz,CDCl3) delta: 8.18 (d, J = 1.8 Hz, 1H), 7.60 (dd, J = 1.8, 8.3 Hz, 1H), 7.48 (d, J = 8.3 Hz, 1H), 6.92 (s, 1H).

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Medshine Discovery Inc.; LUO, Yunfu; BA, Yuyong; CHEN, Shuhui; (135 pag.)EP3567028; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 67832-11-5, 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 67832-11-5 as follows.

4-Bromo-2-bromomethylbenzonitrile (TJA01043) C8H5Br2N MW 274.94. 4-Bromo-2-methylbenzonitrile (5.00 g, 25.5 mmol), N-bromosuccinimide (4.99 g, 28.1 mmol), benzyl peroxide (0.198 g, 0.816 mmol) and carbon tetrachloride (100 mL) were loaded to a r.b. flask and set to reflux (79 C) for 6 h. Once cooled the succinimide was filtered off and carbon tetrachloride removed via a dry ice-acetone cooled rotary evaporator. The residues were dissolved in dichloromethane (100 mL) and washed with distilled H2O (50 mL x 3) and brine (50 mL x 2). Dried over Na2SO4 and solvent removed in vacuo to leave yellow residues. Column chromatography (hexane/dichloromethane 60:40) eluted the title compound as a yellow solid. Recrystallisation (cyclohexane) gave a white crystalline solid (5.07 g, 73 %), mp 61.7-77.2 0C; i?/ 0.30 (hexane/dichloromethane 60:40), c.f. 0.36 (dibromobenzylbromide), 0.36 (4- bromo-2-methylbenzonitrile) ;HPLC (60 % CH3CN in H2O) R, 3.130 (50.62 %), 2.701 (42.38 %, dibromobenzylbromide) ; MS (EI), m/z 274.0 (M- – H, 34 %).

According to the analysis of related databases, 67832-11-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; STERIX LIMITED; WO2007/68905; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

Preparation 15: 2-methyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzamide; Step 1 : 4-bromo-2-methylbenzamide; To a solution of 4-Bromo-2-methylbenzonitrile (3.00 g, 15.3 mmol) in ethanol (9 mL) was added 10% aqueous potassium hydroxide (8.60 mL, 15.3 mmol). The reaction was heated to 8O0C for 16 h. The reaction was cooled to 40C and the precipitated solid was filtered and washed with water to give the title compound as a white solid (2.45 g, 75%). 1H NMR (500 MHz, DMSO-d6) delta ppm 7.71 (bs, 1 H), 7.40 (m, 3H), 7.26 (d, 1 H), 2.31 (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 67832-11-5.

Reference:
Patent; PFIZER INC.; ARHANCET, Graciela Barbieri; CASIMIRO-GARCIA, Agustin; CHEN, Xiangyang; HEPWORTH, David; MEYERS, Marvin Jay; PIOTROWSKI, David Walter; RAHEJA, Raj Kumar; WO2010/116282; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-methylbenzonitrile

To a solution of 4-bromo-2-methylbenzonitrile (2.0 g, 10.2 mmol) in THF (100 ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5 M solution of n-butyl lithium (4.48 ml, 11.2 mmol). The mixture was stirred at -78C for 1h and then poured onto solid carbon dioxide (5 g) in THF (50 ml). The mixture was allowed to warm to room temperature. Water was added (200 ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HCl and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgSO4, and concentrated in vacuo to give a white solid identified as 4-cyano-3-methylbenzoic acid (1.2 g, 73%).

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; Ferring B.V.; EP1449844; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts