Category: 42872-73-1

42872-73-1, name is 2-Bromo-4-methylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 2-Bromo-4-methylbenzonitrile

F. Methyl 3-(4-cyanobenzyloxy)-5-isoxazolecarboxylate. A mixture of o-bromo-p-tolunitrile (18.8 mmol, 3.69 g), methyl 3-hydroxy-5-isoxazolecarboxylate (18.8 mmol, 2.69 g) and potassium carbonate (25 mmol, 3.5 g) was heated at 50 C. overnight. After cooling to room temperature, the solution was added to 1% citric acid and the precipitate was filtered, washed with water and cold ether several times and dried. Yield 4.2 g (87%). NMR (DMSO-d6): delta 7.90 (d, 2H); 7.68 (d, 2H); 7.18 (s, 1H); 5.43 (s, 2H); 3.90 (s, 3H).

The synthetic route of 42872-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dupont Merck Pharmaceutical Company; US5563158; (1996); A;,
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Some common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-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. Product Details of 42872-73-1

To a solution of compound 1 (19.6 g, 100 mmol) in H2SO4 (80 mL) was added HNO3 (80 mL) at 0 C. The mixture was heated to 60 C. for 1 h, cooled to rt and poured into ice water and extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=3/1) to give the desired product (17.3 g, 71.7 mmol, 71.7%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 42872-73-1, its application will become more common.

Reference:
Patent; CoMentis, Inc.; BILCER, Geoffrey M.; NG, Raymond; (104 pag.)US2016/9706; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 42872-73-1,Some common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-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 mixture of 2-bromo-4-methylbenzonitrile (2.00 g, 10.2 mmol), 5, 5, 5′, 5′- tetramethyl-2,2′-bi(l,3,2-dioxaborinane) (3.06 g, 13.6 mmol) and potassium acetate (3.00 g, 30.6 mmol) in anhydrous DMSO (10 mL), in a sealable flask, was purged with Argon for 20 min before PdChldppfj-Cl ECl? adduct (0.25 g, 0.34 mmol) was added, the flask was sealed and the reaction heated at 80 C. After 17 hrs, the reaction was cooled to RT before being partitioned between EtOAc and brine. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried (MgS04), filtered and concentrated in vacuo to afford a brown oil which solidified upon standing. Purification by Isco chromatography afforded 301 A as an off-white solid (1.96 g; 84% yield). NMR (400MHz, DMSO-d6) d 7.72 – 7.63 (m, 2H), 7.43 (dd, 7=7.9, 1.1 Hz, 1H), 3.79 (s, 4H), 2.38 (s, 3H), 0.98 (s, 6H).

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-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BALOG, James Aaron; MARKWALDER, Jay A.; SHAN, Weifang; WILLIAMS, David K.; NARA, Susheel Jethanand; ROY, Saumya; THANGAVEL, Soodamani; CHERUKU, Srinivas; SISTLA, Ramesh Kumar; (230 pag.)WO2020/23355; (2020); A1;,
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Electric Literature of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

{4-methyl-2-[(propan-2-yl)amino]phenyl}(phenyl)methanaminium chloride – The titled compound was obtained following the modified procedure described in WO2006035157 (Protocol A). The starting material 2-(isopropylamino)-4- methylbenzonitrile was prepared from 2-bromo-4-methylbenzonitrile using a Ex.77 Buchwald-Hartwig reaction (2-bromo-4-methylbenzonitrile (1 eq.), isopropylamine (1 .5 eq.), BINAP (0.05 eq.), Pd2(dba)3 (0.03 eq.), Cs2C03 (2 eq.) in toluene at 90C for 6h) – Yield: 43% ; appearance: pale yellow solid ; 1 H NMR, d (ppm) (Methanol d4) : 1 .06 (d, 3H, J=6.2Hz); 1.15 (d, 3H, J=6.2Hz); 2.25 (s, 3H); 3.51 -3.58 (m, 1 H); 5.88 (s, 1 H); 6.61 (s, 2H); 7.25-7.47 (m, 6H); 8.94 (br s, 3H)

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-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GENFIT; DELHOMEL, Jean-Francois; WALCZAK, Robert; MAJD, Zouher; PIHAN, Emilie; BONNET, Pascal; PERSPICACE, Enrico; (198 pag.)WO2016/102633; (2016); A1;,
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Synthetic Route of 42872-73-1, These common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-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.

[0803] 0.545 g (2.70 mmol) of 2-bromo-4-methylbenzo- nitrile, 1.87 g (2.70 mmol, 61% purity, 1 eq.) of tert-butyl 4-methoxy-2-[5-methoxy-2-oxo-4-(4,4,5,5-tetramethyl- 1,3, 2-dioxaborolan-2-yl)pyridin-1 (2H)-yl]butanoate (racemate) and 1.12 g (8.08 mmol, 3 eq.) of potassium carbonate were initially charged in 27 ml of dioxane under argon, 66 mg (0.08 mmol, 0.03 eq) of [1,1 -bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex were added, and the mixture was stirred at 80 C. for 16 h. The reaction mixture was cooled and filtered through kieselguhr, and the filtercake was washed with dichloromethane and acetonitrile. The filtrate was concentrated and the residue was then purified by means of normal phase flash chromatography (eluent: cyclohexane/ethyl acetate, 0-70%). Yield:1.04 g (85% purity, 80% of theory).10804] LC/MS [Method 10]: R=1.86 mm; MS (ESIpos):mlz=413 (M+H), 10805] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=7.80 (d, 1H), 7.43 (d, 1H), 7.39 (s, 1H), 7.34 (s, 1H), 6.38 (s, 1H),5.15-5.05 (m, 1H), 3.62 (s, 3H), 3.43-3.35 (m, 1H), 3.23-3.11 (m, 4H), 2.42 (s, 3H), 2.38-2.29 (m, 2H), 1.40 (s, 9H).

Statistics shows that 2-Bromo-4-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 42872-73-1.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
Nitrile – Wikipedia,
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Application of 42872-73-1, 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred solution of Int4.1 (500 mg) in toluene (7.5 ml) was added 2-bromo-4-methylbenzonitrile (1.2 g), Pd2dba3 (140 mg) and rac-BINAP (191 mg). The flask was twice degased and backfilled with argon. The mixture was stirred at r.t. for 5 minutes. Caesium carbonate (2.5 g) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 4h. Further Pd2dba3 (140 mg) and rac-BINAP (191 mg) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 2h. Water was added and the reaction mixture was extracted with a mixture of dichloromethane and methanol (10:1). The combined organic phases were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 205 mg of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm]= 1.46 (s, 9H), 2.35 (s, 3H), 6.96 (dd, 1H), 7.54 (d, 2H), 7.57 – 7.63 (m, 2H), 7.66 (d, 2H), 7.79 (s, 1 H), 7.87 (dd, 1 H), 9.04 (dd, 1 H), 9.34 (s, 1 H), 9.47 (s, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Schering Pharma AG; EP2343295; (2011); 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-Bromo-4-methylbenzonitrile

2-(2,5-Dimethoxypyridin-4-yl)-4-methylbenzonitrile 2.50 g (9.36 mmol) of diisopropyl (2,5-dimethoxypyridin-4-yl)borate, 3.88 g (28.08 mmol, 3 eq.) of potassium carbonate and 0.764 g (0.936 mmol, 0.1 eq.) of [1,1-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct were initially charged in a flask, which was then evacuated and filled with argon three times. 2.27 g (11.23 mmol, 1.2 eq) of 2-bromo-4-methylbenzonitrile and 68 ml of dioxane were added, argon was passed through for 2 min and the mixture was stirred at 100 C. overnight. The reaction mixture was filtered through kieselguhr and washed with dichloromethane/methanol 9:1, and the filtrate was concentrated. The crude product was purified by means of Biotage-Isolera (eluent: cyclohexane/ethyl acetate, 0-40%). Yield: 1.72 g (71% of theory). LC/MS [Method 1]: Rt=1.00 min; MS (ESIpos): m/z=255 (M+H)+, 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=8.03 (s, 1H), 7.81 (d, 1H), 7.42 (d, 1H), 7.37 (s, 1H), 6.78 (s, 1H), 3.85 (s, 3H), 3.78 (s, 3H), 2.42 (s, 3H).

The synthetic route of 42872-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; STAMPFUss, Jan; (82 pag.)US2017/298052; (2017); 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. 42872-73-1, name is 2-Bromo-4-methylbenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-4-methylbenzonitrile

General procedure: To a stirred mixture of Ar-X (1, 1.0 mmol) and lithium bromide (208 mg, 2.4 mmol) in THF (3.5mL) was added dropwise a solution of i-PrMgBr in THF (2.0 M, 0.53 mL, 1.06 mmol) at -40C under Ar and the resulting mixture was stirred at -40C for 10 min and at room temperature for 3 h. To a stirred solution of dibromodifluoromethane (CF2Br2) in THF (4.90 M, 0.49 mL and 2.4 mmol) was added dropwise the prepared solution of ArMgBr 2 in THF via cannula at between room temperature and 35C over 1 min. and the resulting solution was stirred for 1 h. The reaction was quenched with saturated aqueous NH4Cl (10 mL) and extracted with EtOAc (10 mL¡Á3). The combined extracts were dried over Na2SO4. Concentration of the solvent in vacuo afforded a residue, which was purified by silica gel column chromatography (hexane/EtOAc=10/1) and recycle GPC to give alpha,alpha-dibromo-alpha-fluorotoluene derivative 8.

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; Shiosaki, Masahiro; Inoue, Munenori; Journal of Fluorine Chemistry; vol. 175; (2015); p. 160 – 168;,
Nitrile – Wikipedia,
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Electric Literature of 42872-73-1, A common heterocyclic compound, 42872-73-1, name is 2-Bromo-4-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 2-bromo-4-methylbenzonitrile (4.0 g; 20.40 mmol) in sulfuric acid (6mL) at 0C was added potassium nitrate (2.063 g; 20.40 mmol) in sulfuric acid (18mL). After stirring at 0C for 1.5 hour, the reaction mixture was poured into 500 mL ofice water. The precipitate was collected by filtration and washed with copious amountsof water. The precipate was dried to give 4.5 g (9 1%) of intermediate 455.

The synthetic route of 42872-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 42872-73-1, name is 2-Bromo-4-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 42872-73-1, Product Details of 42872-73-1

To a stirred solution of lnt4.1 (500 mg) in toluene (7.5 ml) was added 2-bromo-4-methylbenzonitrile (1.2 g), Pd2dba3 (140 mg) and rac-BlNAP (191 mg). The flask was twice degased and backfilled with argon. The mixture was stirred at r.t. for 5 minutes. Caesium carbonate (2.5 g) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 4h. Further Pd2dba3 (140 mg) and rac-BINAP (191 mg) was added, the flask was twice degased and backfilled with argon and the mixture was heated to reflux for 2h. Water was added and the reaction mixture was extracted with a mixture of dichloromethane and methanol (10:1). The combined organic phases were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 205 mg of the title compound. 1H-NMR (400MHz, DMSO-d6): delta [ppm]= 1.46 (s, 9H), 2.35 (s, 3H), 6.96 (dd, 1 H), 7.54 (d, 2H), 7.57 – 7.63 (m, 2H), 7.66 (d, 2H), 7.79 (s, 1H), 7.87 (dd, 1H), 9.04 (dd, 1 H), 9.34 (s, 1 H), 9.47 (s, 1 H).

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-4-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bayer Schering Pharma AG; EP2343297; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts