Category: 41963-20-6

Reference of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-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.

To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Bromo-3-methylbenzonitrile

Preparations 27-31 are prepared essentially as described for Preparation 26 using the appropriate boronic acid and l-(3-bromo-pyridin-2-yl)-piperazine.Preparation 32: 3-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzonitrile Stir together 4-bromo-3-methylbenzonitrile (5.20 mmol, 1.02 g), bis(pinacolato) diboron (5.62 mmol, 1.43 g), potassium acetate (15.6 mmol, 1.53 g), and palladium acetate (0.16 mmol, 40 mg) in dry N,N-dimethylformamide (20 mL). Purge the reaction for 30 min. then heat to 85 0C overnight. Partition between water (100 mL) and ethyl acetate (100 mL), wash aqueous layer with ethyl acetate (100 mL). Combine ethyl –50-acetate washings and dry over magnesium sulfate, filter and concentrate in vacuo. Purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:isohexane) to give the title preparation as a white powder (560 mg, 44% yield). MS (ES): m/z = 244 [M+H]+.

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 41963-20-6, name is 4-Bromo-3-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 41963-20-6, Recommanded Product: 4-Bromo-3-methylbenzonitrile

To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-3-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

Example 244A 4-bromo-3-methylbenzylamine LiAlH4 (0.68 g) in diethyl ether (30 mL) was treated with 4-bromo-3-methylbenzonitrile (15 mmol) and refluxed for 2 hours. The mixture was cooled to 0 C. and treated in succession with water (0.7 mL), 20% NaOH (0.5 mL), and water (2.5 mL). The mixture was filtered through a celite pad and the filter cake was washed several times with diethyl ether. The filtrate was dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. MS (ESI+) m/z 194 (M+H)+; MS (ESI-) m/z 192 (M-H)-; 1H NMR (DMSO, 300 MHz) delta 3.97 (s, 2H), 7.30 (m, 1H), 7.46 m, 2H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-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 4-bromo-3-methyl-benzonitrile (commercially available) (500 mg) in dichloromethane (7.5 ml) was added at 00C to a solution of diisobutylaluminium hydride (“DIBAL-H”) (2.6. ml) in hexanes (IM). The reaction mixture was stirred at 00C for 2 hours. The reaction mixture was poured on a mixture of ice (10 g) and aqueous hydrobromic acid (6M) (10 ml). The mixture was allowed to warm to ambient temperature and then extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate, and concentrated to give 4-bromo-3-methyl-benzaldehyde (0.419 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3): 9.95 (s, IH), 7.72 (m, 2H), 7.55 (d, IH), 2.50 (s, 3H) ppm.

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-3-methylbenzonitrile, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; EL QACEMI, Myriem; BOBOSIK, Vladimir; RENOLD, Peter; CASSAYRE, Jerome, Yves; JUNG, Pierre, Joseph; WO2010/20521; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-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.

To a solution of 17 (10.0 g, 49.5 mmol) in carbon tetrachloride (200 mL) were added N-bromosuccinimide (8.81 g, 49.5 mmol) and 2,2′-azobis(isobutyronitrile) (414 mg, 5 mol %), and the mixture was refluxed for 3 h. Water was added, and the mixture was extracted with chloroform. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added dimethylformamide (150 mL) and sodium acetate (20.5 g, 250 mmol), and the mixture was stirred at 80 C. overnight. Water was added, and the mixture was extracted with ether. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue was added methanol (150 mL) and 1 mol/L sodium hydroxide (50 mL), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated to about a third of volume under reduced pressure. Water and hydrochloric acid were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (3:1 hexane/ethyl acetate) followed by trituration with dichloromethane to give 2-bromo-5-cyanobenzyl alcohol (4.63 g, overall 44%): 1H NMR (300 MHz, DMSO-d6) delta (ppm) 4.51 (d, J=5.9 hz, 2H), 5.67 (t, J=5.6 Hz, 1H), 7.67 (dd, J=8.2, 2.0 Hz, 1H), 7.80 (s, J=8.2 Hz, 1H), 7.83 (d, J=2.0 Hz, 1H).

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anacor Pharmaceuticals; US2007/265226; (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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H6BrN

Preparations 27-31 are prepared essentially as described for Preparation 26 using the appropriate boronic acid and l-(3-bromo-pyridin-2-yl)-piperazine.Preparation 32: 3-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzonitrile Stir together 4-bromo-3-methylbenzonitrile (5.20 mmol, 1.02 g), bis(pinacolato) diboron (5.62 mmol, 1.43 g), potassium acetate (15.6 mmol, 1.53 g), and palladium acetate (0.16 mmol, 40 mg) in dry N,N-dimethylformamide (20 mL). Purge the reaction for 30 min. then heat to 85 0C overnight. Partition between water (100 mL) and ethyl acetate (100 mL), wash aqueous layer with ethyl acetate (100 mL). Combine ethyl –50-acetate washings and dry over magnesium sulfate, filter and concentrate in vacuo. Purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:isohexane) to give the title preparation as a white powder (560 mg, 44% yield). MS (ES): m/z = 244 [M+H]+.

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); 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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-3-methylbenzonitrile

(E)-methyl 3-(4-cyano-2-methylphenyl)acrylateTo a solution of 4-bromo-3-methylbenzonitrile (0.784 g, 4 mmol) in DMF (20 ml_) was added methyl acrylate (1.812 ml_, 20.00 mmol), DIPEA (1.747 ml_, 10.00 mmol), Pd(OAc)2(0.090 g, 0.400 mmol) and tri-o-tolylphosphine (0.243 g, 0.800 mmol). The reaction mixture was then heated with microwave irradiation at 150 C under N2atmosphere for 1 h. The reaction mixture was evaporated under vacuum to remove remaining methyl acrylate, then diluted with H20 (20 ml_), extracted with EtOAc (3 x 40 ml_). The combined organic layer was washed with brine (50 ml_), dried over MgS04, filtered, evaporated down under vacuum, and purified by flash chromatography to afford desired product (E)-methyl 3-(4-cyano-2-methylphenyl)acrylate (0.8815 g, 4.38 mmol, 110 % yield). H-NMR (400 MHz, CHLOROFORM-d) delta ppm 2.47 (s, 3 H) 3.84 (s, 3 H) 6.43 (d, J=15.81 Hz, 1 H) 7.47 – 7.55 (m, 2 H) 7.61 (d, J=8.53 Hz, 1 H) 7.92 (d, J=15.81 Hz, 1 H).

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 41963-20-6, name is 4-Bromo-3-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 41963-20-6, COA of Formula: C8H6BrN

Example 4Reductive Elimination from Pd-F ComplexesGeneral Procedure. In a nitrogen-filled glovebox, a screw-cap NMR tube was charged with (BrettPhos)Pd(Ar)(F) complex, aryl bromide (where applicable) and toluene. The tube was capped and taken out of the box and standard (p-fluorotoluene) was added via syringe. In a Varian 500 spectrometer, a broadband gXH probe was tuned to 19F and heated to 100¡ã C. Over the course of 2-3 h, a 19F-NMR spectrum was obtained every 5 minutes with 5 minutes acquisition time per spectrum. Every spectrum was normalized to the standard to account for differences in the tuning of the NMR probe. Reductive Elimination of 5. See FIG. 14. a) 10 mg (BrettPhos)Pd(2-Me,4-CNC6H3)(F) (13 mummol), 1 mL toluene. The fitted curve shows t1/2=14 min. b) 10 mg (BrettPhos)Pd(2-Me,4-CNC6H3)(F) (13 mummol), 12.5 mg ArBr (64 mummol, 5 eq), 0.6 mL toluene. c) The fitted curve shows t1/2=18 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Massachusetts Institute of Technology; US2011/15401; (2011); 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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

Step F tert-Butyl 4-(4-cyano-2-methylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate. A mixture of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (0.40 g, 0.0013 mol), 4-bromo-3-methylbenzonitrile (0.30 g, 0.0016 mol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1, 0.063 g, 0.000078 mol) and potassium carbonate (0.54 g, 0.0039 mol) in N,N-dimethylformamide (6.0 mL, 0.077 mol) was stirred under nitrogen at 80 C. overnight. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried and concentrated. The product was purified by CombiFlash using hexane/EtoAc (max. EA 30%) LC-MS: 299.2 (M+H)+

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 41963-20-6.

Reference:
Patent; Burns, David M.; Yao, Wenqing; He, Chunhong; US2005/250789; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts