Category: 124289-21-0

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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 124289-21-0

3-Methyl-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile Tetrabutylammonium fluoride (3.2 mL, 1M in THF, 3.2 mmol) was added to a mixture of 3-bromo-5-methylbenzonitrile (394 mg, 2.01 mmol), 2-methyl-4-[(trimethylsilyl)ethynyl]-1,3-thiazole (605 mg, 3.10 mmol), triethylamine (0.60 mL, 4.3 mmol), copper (I) iodide (76 mg, 0.40 mmol), dichlorobis(triphenylphosphine)palladium(II) (138 mg, 0.20 mmol), and N,N-dimethylformamide (4 mL). Nitrogen was bubbled through the resulting mixture for 15 min, and the reaction was heated in a microwave reactor at 100 C. for 15 min. The solvent was removed in vacuo, and the resulting residue was chromatographed on silica gel with hexanes:EtOAc (9:1?1:1) to afford 3-methyl-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]benzonitrile as an off-white solid. 1H NMR (CDCl3, 500 MHz) delta 7.63 (s, 1H), 7.58 (s, 1H), 7.43 (s, 1H), 7.42 (s, 1H), 2.75 (s, 3H), 2.39 (s, 3H). MS (ESI) 239.5 (M++H).

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; US2007/60618; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-methylbenzonitrile

a) Preparation of Compound 43B (0368) To a solution of 3-bromo-5-methylbenzonitrile (1.0 g, 5.12 mmol) in MeOH (40 mL) was added NiCl2.6H2O (121 mg, 0.51 mmol), Boc2O (1.35 g, 6.20 mmol) and NaBH4 (780 mg, 20.5 mmol) at -20 C. Then the mixture was stirred for 2 hrs at 0-10 C. The reaction solution was quenched with sat. NH4Cl (120 mL), diluted with H2O (200 mL) and extracted with EA (100 mL×3). The combined organic layers were washed by brine (50 mL×2), dried over Na2SO4 and concentrated to give tert-butyl 3-bromo-5-methylbenzylcarbamate (Compound 43B, 1.3 g, 86.7%) as a white solid. MS: calc’d 300 (M+H)+, measured 300 (M+H)+.

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Hoves, Sabine; Wang, Lisha; Yun, Hongying; Zhang, Weixing; Zhu, Wei; (58 pag.)US2016/257653; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6BrN

Example 46 3-Bromo-5-(bromomethyl)benzonitrile A mixture of 3-bromo-5-methylbenzonitrile (9.80 g, 45.0 mmol), NBS (8.90 g, 45.0 mmol) and BPO (0.40 g) in CCl4 (250 mL) was heated for 10 h at reflux. The reaction mixture was cooled to room temperature and filtered, and the organic phase was washed successively with saturated sodium bicarbonate (100 mL), water (2*50 mL) and brine (2*50 mL). The combined organic phases were dried over Na2SO4 and concentrated in vacuum to give 12.5 g of crude 3-bromo-5-(bromomethyl)benzonitrile.

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Glaxo Group Limited; US2009/203677; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-methylbenzonitrile

3-Bromo-5-hydroxymethylbenzonitrile(4); 3-Bromo-5-methylbenzonitrile(15g, 76 5mmol) was refluxed with N-bromo succiotaniotamiotade(13 6g, 76 5mmol) and benzoyl peroxiotade(925mg, 3 8mmol) in CCI4(I OOmI) under a light of 500W tungsten lamp After 4hr the mixture was cooled to room temperature, filtered, and concentrated The residue was stirred with sodium acetate(9 41 g, 115mmot) in DMF(100ml) for overnight at room temperature The mixture was diluted with ether, washed with water three times, dried with MgSO4, filtered, and evaporated in vacuo The residue was stirred with ammonium hydroxiotade(30ml) in methanol(IOOml) at room temperature After 3hr , the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography(eluent, ethyl acetate hexane(1 4)) to afford 7 1g(44% overali) of the title compound as a white solid m p 108-109 0C1H-NMR(200MHz, CDCI3) delta 2 03(1 H, t, J=5 6Hz), 4 73(2H, d, J=5 6Hz), 7 60(1 H1 s), 7 70(1 H, s), 7 76(1 H, s) m/z (El) 212 (M+)

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KIM, Choung, U.; MITCHELL, Michael, L.; SON, Jong, Chan; WO2010/9047; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 124289-21-0, name is 3-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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: C8H6BrN

In a vial fitted with a stir bar was placed 3-bromo-5-methyl-benzonitrile (266 mg, 1.357 mmol), 1-(3,5-difluorophenyl)-1,2,4-triazol-3-amine (205 mg, 1.045 mmol), sodium tert-butoxide (106 mg, 1.103 mmol), and chloro(2-di-t- butylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)[2-(2- aminoethyl)phenyl]palladium(II) (t-BuXPhos Palladacycle) (30 mg, 0.04607 mmol). tert-Butanol (5 mL) was added and the vial was sealed and purged with nitrogen. The mixture was heated to 80 C overnight. The reaction was extracted with ethyl acetate and washed with water. The organics were treated with MP-TMT (ca 100 mg) and refluxed for 4 hours, to capture residual palladium. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude 3-[[1-(3,5-difluorophenyl)-1,2,4-triazol-3-yl]amino]-5-methyl-benzonitrile (0.35 g of 90% purity, 97%). A small sample of crude material was crystalized from acetonitrile to give analytically pure 3-[[1-(3,5-difluorophenyl)-1,2,4-triazol-3-yl]amino]-5-methyl-benzonitrile. MR (300 MHz, DMSO-d6) delta 9.94 (s, 1H), 9.21 (s, 1H), 7.84 (s, 1H), 7.76 – 7.52 (m, 3H), 7.38 – 7.20 (m, 1H), 7.15 (s, 1H), 2.35 (s, 3H) ppm. ESI- MS m/z calc. 31 1.09827, found 312.15 (M+l)+; Retention time: 0.95 minutes

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 124289-21-0, its application will become more common.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; BETHIEL, Randy Scott; CAO, Jingrong; COLLIER, Philip, N.; DAVIES, Robert J.; DOYLE, Elisabeth; FRANTZ, James Daniel; GOLDMAN, Brian Anthony; GREY, Ronald Lee; GRILLOT, Anne-laure; GU, Wenxin; KOLPAK, Adrianne Lynne; KRAUSS, Paul Eduardo; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MESSERSMITH, David; PEROLA, Emanuele; RYU, Elizabeth, Jin-Sun; SYKEN, Joshua; WANG, Jian; (491 pag.)WO2018/106646; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 124289-21-0,Some common heterocyclic compound, 124289-21-0, name is 3-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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 solution of 1 -(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), , 3-bromo-5- methylbenzonitrile (24 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2003 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H20 (4:1, 2.1 mL) was heated at 85 C for 18 hours. Water (5 mL) was added and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (2 to 5%) and afforded the title compound (22 mg, 0.039 mmol, 38%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-methylbenzonitrile, its application will become more common.