Category: 75344-77-3

Electric Literature of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Step A: 4-bromo-3.5-dimethylbenzamide To a solution of 4-bromo-3, 5- dimethylbenzonitrile (1.0 g, 4.8 mmol) in DMSO (10 ml) at 0 C was added 35% H202 (0.542 mL, 6.19 mmol) and K2C03 (1.32 g, 9.52 mmol). The resulting mixture was stirred at 20 C for2 hours and then poured into water (50 mL). The resulting solid was collected by filtration, then washed with water twice, dried in an oven to give the title compound. ?H NMR (400MHz, CD3OD) oe: 7.62 (s, 2H), 2.46 (s, 6H).

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; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkattle; COLLETTI, Steven, L.; DANG, Qun; DHONDI, Pawan, K.; GUDE, Candido; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar, G.; NARGUND, Ravi, P.; YANG, De-Yi; XIAO, Dong; ZHU, Cheng; WO2015/73342; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 75344-77-3, 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed 4-bromo-3,5-dimethylbenzonitrile (4 g, 19.04 mmol, 1.00 equiv) and dichloromethane (50 mL). This was followed by the addition of diisobutylaluminum hydride (40 mL) dropwise with stirring at -65C. The resulting solution was stirring for 2 h at room temperature. To the reaction mixture was added hydrogen chloride (5%, 40 mL) dropwise with stirring at room temperature. The resulting solution was heated to reflux for 30 min and then cooled to room temperature. The resulting solution was diluted with 200 mL of DCM. The organic layer was washed with 3×100 mL of brine and then dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 4 g (crude) of 4- bromo-3,5-dimethylbenzaldehyde as light yellow oil.

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, 4-Bromo-3,5-dimethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERIAL, INC.; LONG, Alan; LEE, Hyoung, Ik; (185 pag.)WO2019/36407; (2019); 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromo-3,5-dimethylbenzonitrile

Under a nitrogen atmosphere, Add the previous step in a 250 ml three-neck round bottom reaction bottle. 10-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, 420 mg of 4-bromo-3,5-dimethylbenzonitrile, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 molar solution of potassium carbonate per liter, Stir and dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. The yield of the solid product was finally 77%.

According to the analysis of related databases, 75344-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C9H8BrN

To a solution of 4-bromo-3,5-dimethylbenzonitrile (1 g) in N,N-dimethylformamide (10 ml_) is added NH4CI (770 mg) and NaN3 (800 mg) and the mixture is heated to 100C for 12 hours. After cooling to room temperature the mixture is diluted with water. The formed precipitate is filtered off, washed with water and dried to give the title compound. Yield: 650 mg; Mass spectrum (ESI+): m/z = 253 [M+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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144097; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Step A: 4-bromo-3.5-dimethylbenzamide To a solution of 4-bromo-3, 5- dimethylbenzonitrile (1.0 g, 4.8 mmol) in DMSO (10 ml) at 0 C was added 35% H202 (0.542 mL, 6.19 mmol) and K2C03 (1.32 g, 9.52 mmol). The resulting mixture was stirred at 20 C for2 hours and then poured into water (50 mL). The resulting solid was collected by filtration, then washed with water twice, dried in an oven to give the title compound. ?H NMR (400MHz, CD3OD) oe: 7.62 (s, 2H), 2.46 (s, 6H).

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; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkattle; COLLETTI, Steven, L.; DANG, Qun; DHONDI, Pawan, K.; GUDE, Candido; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar, G.; NARGUND, Ravi, P.; YANG, De-Yi; XIAO, Dong; ZHU, Cheng; WO2015/73342; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, 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. category: nitriles-buliding-blocks

Step 1 : Synthesis of 4-cyano-2,6-dimethylphenylboronic acid pinacol ester First, 5.0 g (24 mmol) of 4-bromo-3,5-dimethylbenzonitrile, 7.3 g (29 mmol) of bis(pinacolato)diboron, 8.4 g (86 mmol) of potassium acetate, and 120 mL of dimethyl sulfoxide (DMSO) were put into a three-neck flask, and the atmosphere in the flask was replaced with nitrogen. To this mixture were added 0.20 g (0.24 mmol) of [l, l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct and 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and the mixture was heated and stirred at 90 C for 7 hours. To this mixture were further added 0.20 g (0.24 mmol) of [l,l’-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct, 0.20 g (0.48 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 3.5 g (14 mmol) of bis(pinacolato)diboron were further added to, and the mixture was heated and stirred at 100 C for 17 hours to be reacted. Water was added to the reacted solution to separate the solution into an organic layer and an aqueous layer, and the aqueous layer was subjected to extraction with toluene. A solution obtained by combining the organic layer and the solution of the extract was washed with water and saturated saline, and anhydrous magnesium sulfate was added thereto for drying. The obtained mixture was subjected to gravity filtration, and the filtrate was concentrated to give a solid. This solid was purified by flash column chromatography. As developing solvents, first, a mixed solvent of toluene and ethyl acetate in a ratio of 10: 1 (v:v) was used, and then a mixed solvent of toluene and ethyl acetate in a ratio of 5: 1 (v:v) was used. The obtained fraction was concentrated to give a solid. This solid was washed with toluene and hexane, so that 3.5 g of a white solid was obtained in a yield of 57 %. The obtained white solid was identified as 4-cyano-2,6-dimethylphenylboronic acid pinacol ester by nuclear magnetic resonance ( MR) spectroscopy. The synthesis scheme of Step 1 is shown in (a-9) below.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SEMICONDUCTOR ENERGY LABORATORY CO., LTD.; SEO, Satoshi; WATABE, Takeyoshi; INOUE, Hideko; YAMADA, Yui; MITSUMORI, Satomi; TAKAHASHI, Tatsuyoshi; HARA, Tomoka; (444 pag.)WO2016/203350; (2016); 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-3,5-dimethylbenzonitrile

Example 2; Preparation of (S)-2-tert-Butoxvcarbonvlamino-3-(4-cvano-2,6-dimethvl- phenvD-propionic acid methyl esterA 5OmL three-necked round bottom flask equipped with an addition funnel, magnetic stirrer, heating mantel, and thermocouple was charged under nitrogen dry DMAc (2mL), I2 (38.1 mg, 0.15mmol) and zinc powder activated (washed with 10% HCI, rinsed with H2O and acetone) (393 mg, 6 mmol). The resulting mixture was stirred at 23C until the red color of I2 disappeared (2 minutes). A solution of Boc-beta-iodo-L-alanine methyl ester (1 g, 3mmol) in DMAc (2 ml.) was added slowly, (temperature change from 210C to 29C) and the resulting mixture was stirred at 8O0C for 0.5-1 hour, then co cooled to 35C. To the resulting mixture were added, successively, 4-bromo-3,5-dimethyl- benzonithle (315 mg, 1.5mmol) in DMAc (6ml_), P(o-tol)3 (36.5 mg, 0.12 mmol) and Pd2(dba)3 (55 mg, O.Odeltammol). The resulting mixture was heated to 700C, with stirring for 1 hour, then cooled to ambient temperature. The resulting mixture was diluted with EtOAc (15ml_) and filtered with STAND SUPER-CEL 815520. The EtOAc solution was quenched with 1 N HCI (4OmL) and extracted with ethyl acetate (2OmL). The combined organic phases were washed with H2O (2 x 5OmL) and then with 50% brine, dried over Na2SO4 , filtered and evaporated to dryness in vacuo to yield a brown solid. The title compound was crystallized from EtOAc (5mL) and heptane (4OmL) to yield a white solid.

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.

Synthetic Route of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

3-(4-Bromo-3,5-dimethyl-phenyl)-1H-tetrazole 4-Bromo-3,5-dimethyl benzonitrile (3.0 g, 14.3 mmol), sodium azide (2.32 g, 35.7 mmol) and ammonium chloride (2.3 g, 42.84 mmol) are suspended in dry N,N-dimethylformamide and heated at 140 C. for 7 hours. The mixture is allowed to cool to room temperature, diluted with water and the precipitated solid collected by filtration, washed with water and dried to give the title compound (yield 1.74 g). The mother liquor was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic extracts were combined and the solvent removed to give a second crop of title compound (yield 1.39 g, total yield 3.13 g). LC (MIL-07-002): tR=0.83 min; Mass spectrum (ES+): m/z=253/255 [M+H]+.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 75344-77-3,Some common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

Under a nitrogen atmosphere, Add 420 mg to a 250 ml three-neck round bottom reaction bottle4-bromo-3,5-dimethylbenzonitrile and 10-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10H-phenoxazine, Then, 120 ml of toluene, 40 ml of absolute ethanol and 40 ml of a 2 mol-liter potassium carbonate aqueous solution were sequentially added thereto, followed by stirring to dissolve. After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming. The reaction system was extracted with a dichloromethane solvent. It was washed three times with deionized water, three times with saturated brine, and dried over anhydrous magnesium sulfate for 1 hour. Purification of the product by column chromatography, The eluent is a mixed solvent of petroleum ether and dichloromethane in a ratio of 3:1. Finally, a white solid product was obtained with a yield of 69%.

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-3,5-dimethylbenzonitrile, its application will become more common.

Reference:
Patent; South China University of Technology; Su Shijian; Cai Xinyi; Qiu Weidong; Qiao Zhenyang; (32 pag.)CN108530376; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 75344-77-3, 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

4-Bromo-3,5-dimethyl benzonitrile (5.0 g) is dissolved in HCl in dioxane (4 M, 17.3 mL) and EtOH (5 mL) added. After stirring for 16 h volatiles are evaporated in vacuo and the crude residue (6.5 g) used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3,5-dimethylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts