Category: 57381-37-0

These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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. Product Details of 57381-37-0

To a solutionof 2-bromo-5-chlorobenzonitrile (20 g, 93 mmol) in THF (200 mL) was added cyclopropylmagnesiumbromide (558 mL, 279 mmol) at 0 C. The resulting reaction – 151 -mixture was stirred at 0-5 C for 5 hours before MeOH (100 mL) was added and stirring continued at room temperature for 15 min. NaBH4 (7.1 g, 186 mmol) was added subsequently and the reaction mixture was stirred at room temperature overnight. Water was added and reaction mixture was exacted with AcOEt (300 mL x 3). The combined organic layers were concentrated in vacuo to give a crude product which was then purified by chromatography to give (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (8.2 g, yield 34%).

The synthetic route of 2-Bromo-5-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
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Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. category: nitriles-buliding-blocks

To a stirred solution of 2-bromo-5-chlorobenzonitrile (80 g, 370 mmol) in THF (1000 mL)at 0C was added EtMgBr (370 mL, 1110 mmol) dropwise. The reaction mixture wasstuffed at 0-5C for 5 hours before MeOH (500 mL) was added dropwise. After the solution was stuffed for another 15 mi NaBH4 (28 g, 740 mmol) was added carefully and the resulting mixture was stirred at room temperature for 16 hours. The reaction solution was then poured into water and exacted with EtOAc (3 x). The combined organic layerswere dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product, which was purified by column chromatography (petroleum ether: EtOAc =3: 1) to afford the title compound (30 g, 34.6%) as yellowish oil. MS: 235.5 [M+Hj.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-37-0, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; ZHOU, Mingwei; WO2014/191338; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. HPLC of Formula: C7H3BrClN

A microwave reaction vessel was charged with (3-(ethoxycarbonyl)phenyl)boronic acid (427 mg, 2.2 mmol), 2-bromo-5-chlorobenzonitrile (433 mg, 2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (82 mg, 0.2 mmol), potassium phosphate tribasic (1.27 g, 6 mmol), and palladium(II) acetate (22.5 mg, 0.1 mmol) and was sealed. It was put under vacuum and filled with argon (3x repeated). Then the degassed toluene was added and the suspension was stirred at 80C for 2 hours. The reaction mixture was then allowed to cool to room temperature, diluted with 5 ml EtOAc and filtered through a thin bed of silica (0.3-0.5 mm) and eluted/washed with EtOAc (ca. 40 ml) and concentrated under reduced pressure. After Si02 flash chromatography, ethyl 4′-chloro-2′-cyano-[1,1′-biphenyl]-3-carboxylate was obtained as a off-white, crystalline solid (481 mg, 84.2%). MS (ESI): m/z = 286.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-37-0, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BLEICHER, Konrad; HERT, Jerome; KROLL, Carsten; DEY, Fabian; (77 pag.)WO2018/189063; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-37-0, The chemical industry reduces the impact on the environment during synthesis 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: S3 (1.5 mmol) was dissolved in NEt3 (5 mL) and degassed for 30 minutes at room temperature. Then PdCl2(PPh3)2 (0.2 mol%), CuI (0.2 mol%) and the alkyne were added to S3/NEt3 solution. The obtained dark brown suspension was stirred for 12 h at 60C. After cooling to room temperature the solvent of the reaction mixture was filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography (petroleum ether : ethyl acetate = 30:1) to provide 1t-1w (in 76-83% yield).

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, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaodong; Deng, Guobo; Liang, Yun; Tetrahedron Letters; vol. 59; 29; (2018); p. 2844 – 2847;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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. COA of Formula: C7H3BrClN

To a solutionof 2-bromo-5-chlorobenzonitrile (20 g, 93 mmol) in THF (200 mL) was added cyclopropylmagnesiumbromide (558 mL, 279 mmol) at 0 C. The resulting reaction – 151 -mixture was stirred at 0-5 C for 5 hours before MeOH (100 mL) was added and stirring continued at room temperature for 15 min. NaBH4 (7.1 g, 186 mmol) was added subsequently and the reaction mixture was stirred at room temperature overnight. Water was added and reaction mixture was exacted with AcOEt (300 mL x 3). The combined organic layers were concentrated in vacuo to give a crude product which was then purified by chromatography to give (2-bromo-5-chlorophenyl)(cyclopropyl)methanamine (8.2 g, yield 34%).

The synthetic route of 2-Bromo-5-chlorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, molecular formula is C7H3BrClN, 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. Quality Control of 2-Bromo-5-chlorobenzonitrile

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)- 1-methyl-ethylamine To a stirred solution of 2-bromo-5-chloro-benzonitrile (10 g, 46 mmol) in THF (200 mL) at 0 C, was added MeMgBr (77 mL, 230 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. Ti(Oi-Pr)4 (13 g, 46 mmol) was added and the solution was stirred for another 16 hours before it was quenched with aq. HC1 solution and washed with EtOAc. The aqueous phase was adjusted to pH ~ 10 with aq. NaOH solution, and exacted with EtOAc (3x). The combined organic layers were concentrated to give a crude title product (3.8 g, 33%) as oil, which was used directly in the next step without further purification. MS: 249.30 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57381-37-0, its application will become more common.

Synthetic Route of 57381-37-0, 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. 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under the protection of nitrogen,To 2-(3-((6-fluoroquinolin-4-yl)oxy)-8-azabicyclo[3.2.1]oct-8-yl)propanamide (100 mg, 0.3 mmol),2-bromo-5-chlorobenzonitrile (63 mg, 0.3 mmol) and NaOH (14 mg, 0.3 mmol) in 2 mL of NMPCuI (6 mg, 0.03 mmol) was added to the solution.The reaction mixture was stirred at 120 C overnight.The reaction system was poured into 10 mL of water.Extract with EA (10 mL x 3).The organic phase is washed with saturated brine.Dry anhydrous Na2SO4 and concentrate under reduced pressure.The residue was chromatographed on silica gel (DCM:MeOH = 10:1)Purification afforded 30 mg (yield: 21%) of the title compound.It is a white solid.

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, 2-Bromo-5-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chengdu Hai Borui Pharmaceutical Co., Ltd.; Chengdu Beite Pharmaceutical Co., Ltd.; Huang Haoxi; Liu Guanfeng; Ren Junfeng; Yi Shoubing; Chen Tonghun; He Quanhong; Wu Xiancai; Li Yingfu; Su Zhonghai; (91 pag.)CN109575022; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-37-0, 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. 57381-37-0 name is 2-Bromo-5-chlorobenzonitrile, 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.

Example 50 : (R)-4 ‘-( 4-Amino-8-methyl-5-oxo-7,8-dihvdropyrimido [5,4- f| [ 1 ,41 oxazepin-6( 5H)-yl)-4-chloro-2 ‘-fluor obiphenyl-2-carbonitrile; (i~)-4-Amino-6-(3-fluoro-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)phenyl)-8- methyl-7,8-dihydropyrimido[5,4-f][l ,4]oxazepin-5(6H)-one (Intermediate 51 ; 290 mg, 0.70 mmol), PdCl2(dppf)-DCM adduct (28.6 mg, 0.04 mmol), potassium phosphate (0.07 mL, 0.84 mmol) and 2-bromo-5-chlorobenzonitrile (182 mg, 0.84 mmol) were suspended in DME (3 mL), ethanol (1.5 mL) and water (0.75 mL) and sealed into a microwave tube, degassed under vacuum and the atmosphere replaced with nitrogen. The reaction was heated to 130 C for 90 minutes in the microwave reactor and cooled to RT. The reaction mixture was evaporated to dryness and redissolved in methyl THF (25 mL), and washed sequentially with water (25 mL) and saturated brine (25 mL). The organic layer was dried over Na2SC”4, filtered and evaporated to afford crude product. The crude product was purified by preparative HPLC (Waters XBridge Prep CI 8 OBD column, 5mu silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (74.0 mg, 24.94 %) as a white solid. 1H NMR (400 MHz, CDC13, 30C) 2.61 (3H, s), 3.89 – 4.00 (2H, m), 4.86 – 5.08 (1H, m), 5.51 – 5.74 (1H, m), 7.22 (1H, d), 7.49 (2H, dd), 7.66 (1H, dd), 7.78 (1H, d), 7.82 – 8.07 (1H, m), 8.33 (1H, s). m/z (ES+), (M+H)+ = 424

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-chlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIRCH, Alan, Martin; GOLDBERG, Frederick, Woolf; LEACH, Andrew; WO2011/121350; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts