Category: 67832-11-5

Application of 67832-11-5, 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. 67832-11-5 name is 4-Bromo-2-methylbenzonitrile, 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.

[0617j To a solution of 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) in anhydrous THF (20 mL) under nitrogen at 0 C was added 1.0 M solution of borane in THF (46 mL). The reaction mixture was stirred at 0 C for 1 h, and heated at 80 C overnight. The reaction mixture was cooled to 0 C and slowly quenched with MeOH, concentrated in vacuo. The crude product was treated with EtOAc (20 mL) and 4 M of HC1 in 1,4-dioxane (8.0 mL, 32 mmol) for 5 mm. The solid was filtered, rinsed with diethyl ether, dried to give the title compound as a white powder (3.24 g, yield: 100%). LCMS: RT 0.75 mm.; MH+ 200.0. ?H NMR (300 MHz, DMSOd6) 5: 8.28 (br. s., 2H), 7.42 – 7.54 (m, 2H), 7.34 (d, J = 7.93 Hz, 1H), 3.99 (d, J = 4.15 Hz, 2H), 2.35 (s, 3H).

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Nitrile – Wikipedia,
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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. Product Details of 67832-11-5

To a solution of 4-bromo-2-methylbenzonitrile (2.0g, 10.2mmol) in THF (100ml) at -78C under a nitrogen atmosphere was added dropwise a 2.5M solution of n-butyl lithium (4.48ml, 11.2mmol). The mixture was stirred at -78C for lh and then poured onto solid carbon dioxide (5g) in THF (50ml). The mixture was allowed to warm to room temperature. Water was added (200ml) and the mixture was extracted with diethyl ether (3 times). The aqueous layer was acidified by addition of concentrated HC1 and extracted with chloroform (3 times). The combined chloroform extracts were washed with water, dried over MgS04, and concentrated in vacuo to give a white solid; yielding (73%).

The synthetic route of 4-Bromo-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FERRING B.V.; WO2006/18443; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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

EXAMPLE 164A 4′-methoxy-3-methyl-1,1′-biphenyl-4-carbonitrile 4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75 C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3*40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85% yield). 1H-NMR (300 MHz, CDCl3) delta2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (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 4-Bromo-2-methylbenzonitrile, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6620839; (2003); B2;,
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

[ TERT-BUTYL 4- (4-CYANO-3-METHYLPHENYL)-3, 6-DIHYDROPYRIDINE-1 (2H)-CARBOXYLATE] [4-BROMO-2-METHYL-BENZONITRILE] (150 mg, 0.77 mmol), tert-butyl [4- (4,] 4, [5,] 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl)-3, [6-DIHYDROPYRIDINE-1] [(2H)-CARBOXYLATE] (284 mg, 0.92 mmol) and [PDCL2] (dppf) (38 mg, [0.] 05 mmol) were dissolved in toluene (2. [5] ml), [ETOH] (0.75 ml) and 2M aqueous [NA2CO3.] The reaction vessel was purged with nitrogen and heated at [80 C] over night. After cooling, the mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over [NA2SO4] and purified using flash chromatography (heptane: [ETHYLACETATE] 7: 1) affording 171 mg (74%) of white crystals. [LC-MS M/Z 199 [M+].] IH NMR [(CDCI3)] : [8] 7.52 [(1H,] d, J=8. 09 Hz); 7.27 [(1H,] s); 7.23 [(1H,] d, [J=8.] 51 Hz); 6.12 [(1H,] bs); 4.07 (2H, q, J=5. 81 Hz); 3.61 (2H, t, J=5. 61 Hz); 2.52 (3H, s); 2.48 (2H, bs); 1.47 (9H, s).

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

Reference:
Patent; ASTRAZENECA AB; WO2004/24718; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 67832-11-5, 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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 2.5 M n-butyllithium in hexanes(6.7 mL, 16.8 mmol) was added to anhydrous THF (15 mL) at -78 C. A solution of 4-bromo-2-methylbenzonitrile 21 (3.0 g, 15.3 mmol) in THF (15 mL) was then added dropwise and allowed to stir for 30 min. Dry ice (solid CO2) was added and the solution was allowed to stir 1 h while warming to room temperature. The reaction was then concentrated in vacuo and the resulting residue was triturated in ether and filtered. The solid was dissolved in EtOAc and washed with 2 M HCl and brine. The organic layer was isolated, dried over MgSO4, concentrated in vacuo, then triturated in ether/ hexane and dried under high vacuum. Obtained 4-cyano-3-methylbenzoic acid 22 (1.5 g, 60.8% yield) as a white solid. 1H NMR (400 MHz, CDCl3) delta (ppm) 8.18 (s, 1H), 8.02-8.09 (m, 1H), 7.75-7.81 (m, 1H), 2.61 (s, 3H).

The synthetic route of 4-Bromo-2-methylbenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yestrepsky, Bryan D.; Xu, Yuanxi; Breen, Meghan E.; Li, Xiaoqin; Rajeswaran, Walajapet G.; Ryu, Jenny G.; Sorenson, Roderick J.; Tsume, Yasuhiro; Wilson, Michael W.; Zhang, Wenpeng; Sun, Duxin; Sun, Hongmin; Larsen, Scott D.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1880 – 1897;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 67832-11-5, 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. 67832-11-5 name is 4-Bromo-2-methylbenzonitrile, 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.

To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL) was added BH3¡¤THF (45 mL, 45 mmol) at 0 C. The solution was stirred for 1 h and heated to 80 C for 2 h. The mixture was quenched with H2O and extracted with EtOAc (50 mL x 3). The organic layer was concentrated in vacuo to afford a residue which was suspended in saturated HCl/EtOAc and filtered. The filter cake was washed with diethyl ether (20 mL x 3) and dried under vacuum to afford the desired product (2.1 g, yield 69%) as white solid. ESI-MS (M+H)+: 200.1.

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

4-bromo-2-methylbenzonitrile (1 mmol) was suspended in water (49 mL) and potassium hydroxide was added (50 mmol); the reaction mixture was stirred at reflux overnight. After cooling, the basic solution was washed with ethyl acetate (3 x 15 mL), acidified with hydrochloric acid (6M) and extracted with ethyl acetate (3 x 15 mL). The organic phase deriving from the acidic extraction was dried over anhydrous sodium sulfate and concentrated in vacuo, yielding the desired product as a white solid. Yield: 60%. TLC (dichloromethane – methanol 9:1): Rf = 0.46. Mp: 182C. 1H-NMR (300 MHz, CD3OD) delta (ppm) 7.80 (d, J = 8.4 Hz, 1H, H6), 7.48 (s, 1H, H3), 7.42 (d, J = 8.4 Hz, 1H, H5), 2.56 (s, 3H, CH3).

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; Chiarelli, Laurent R.; Mori, Matteo; Barlocco, Daniela; Beretta, Giangiacomo; Gelain, Arianna; Pini, Elena; Porcino, Marianna; Mori, Giorgia; Stelitano, Giovanni; Costantino, Luca; Lapillo, Margherita; Bonanni, Davide; Poli, Giulio; Tuccinardi, Tiziano; Villa, Stefania; Meneghetti, Fiorella; European Journal of Medicinal Chemistry; vol. 155; (2018); p. 754 – 763;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts