Category: 42872-83-3

Reference of 42872-83-3, A common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-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.

To a solution of (3-(ethoxycarbonyl)phenyl)boronic acid (386 mg, 1.99 mmol, Eq: 1.3) in THF (5 mL) was added 2-bromo-5-methylbenzonitrile (300 mg, 1.53 mmol, Eq: 1) and potassium fluoride (267 mg, 4.59 mmol, Eq: 3). The reaction mixture was degassed under a slight argon flush in an ultrasonic bath for 15 minutes. palladium(II) acetate (6.87 mg, 30.6 muiotaetaomicron, Eq: 0.02) and (2-biphenyl)di-tert-butylphosphine (18.3 mg, 61.2 muiotaetaomicron, Eq: 0.04) was added. The reaction mixture was stirred for 18 hours at 50C. The reaction mixture was poured on 30 mL water and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by silica gel chromatography to yield ethyl 3-(2-cyano-4-methylphenyl)benzoate as a white solid (383 mg, 94.3%). MS (ESI): m/z = 266.118 [M+H]+.

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

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,
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Related Products of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-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.

MethyI-2-(pyrimidin-2-yl)benzonitrile (2); To a 500 mL three neck round bottom flask, equipped with an overhead stirrer, thermocouple and nitrogen inlet and dropped funnel, was charged 2-bromo-5-methylbenzylnitrile1 (20.00 g) and THF (60 mL, 3 V) and was cooled to -15 C. 1.3 M of i-PrMgCI’LiCl (1 10.0 mL, 1.4 equiv) was slowly added at -15 to -12 C. The reaction mixture was stirred at -15 to -12 C for 3.5 h (> 99 A% conversion). 15.45 g of anhydrous ZnCl2 (1.1 equiv, powder) was added to the Grignard reagent at -12 C in one portion. The reaction was exothermic raising the temperature of the reaction mixture to 0 C. The reaction mixture was stirred at -3 to 2 C for 0.5 h and slowly warmed to rt over 0.5 h. The reaction mixture became a homogenous solution and then 2-chloropyrimidine (15.37 g) was added.To a slurry of 1 mol% Pd(OAc)2 (0.229 g), 4 mol% («-Bu)3P (0.826 g or 1.02 mL) in THF (8 mL) was added 2.0 M of BuMgCl (1.02 mL) THF solution to become yellow cloudy solution, The resulting catalyst solution was added to the reaction mixture. The resulting mixture was heated at 55 C for 17 h: (98 A% conversion). The reaction mixture was solvent-switched to isopropyl alcohol (140 mL, total volume) at 40-45 C. Then 5 wt% NH4C1 aqueous solution (70 mL) was added dropwise at 15 to 20 C. The resulting slurry was aged at 10 C for 5 h. The crystalline solid was collected by filtration, rinsed with cold isopropyl alcohol/water (1 : 1, 35 mL), and ^-heptane (30 mL), dried under vacuum with nitrogen sweep and gave desired product2 (17.33 g, 87% isolated yield, 99.5 LCAP purity).HPLC MethodColumn: Zorbax Eclipse Plus CI 8 50 x 4.6 mm, 1.8 muetaiota particle size, Column Temp.: 25 C; Flow Rate: 1.5 mL/min; Detection: 230 nm; Mobile Phase: A: Water 0.1% H3PO4, B: AcetonitrileMobile Phase Program: Time A0 90%5 min 5%6 min 5%6.1 min 90%8 min 90%Compound 2: 3.19 min

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; FENG, Yun Shao; MOSES, Anthony; ZHONG, Yong-Li; WO2012/58129; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-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.

General procedure: To a mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

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-5-methylbenzonitrile, its application will become more common.

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, belongs to nitriles-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 42872-83-3, HPLC of Formula: C8H6BrN

Scheme VI begins with the bromination Reaction 1 of a 4-bromotoluene XXXII with N-bromosuccinamide (NBS) and benzoyl peroxide in chloroform.

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-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARIAD PHARMACEUTICALS, INC.; ZECH, Stephan, G.; KOHLMANN, Anna; LI, Feng; WANG, Yihan; ZHOU, Tianjun; DALGARNO, David, C.; SHAKESPEARE, William, C.; ZHU, Xiaotian; WO2014/151761; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-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.

General procedure: To a mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 42872-83-3, These common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-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.

General procedure: Ni NPs/HT (0.05 g) is placed in a heavy-walled pressure tube, followed by the addition of water (4 ml) and benzonitrile (1 mmol), and the reaction mixture is vigorously stirred at 120 C in an oil bath for the specified time in tables. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture is extracted with ethyl acetate, after the extraction, the catalyst is removed by filtration, and the filtrate is cooled to 0 C, and white crystals are precipitated from the filtrate. The crystalline product was obtained by simple filtration and dried in vacuo at room temperature to give analytically amide product. In cases where the product not precipitated out, the reaction mixture was extracted with ethyl acetate, subsequent purification by column chromatography on silica gel provided amide product.

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Subramanian, Thirumeni; Pitchumani, Kasi; Catalysis Communications; vol. 29; (2012); p. 109 – 113;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts