Category: 64829-31-8

Application of 64829-31-8, A common heterocyclic compound, 64829-31-8, name is 3-Methoxy-4-methylphenylacetonitrile, molecular formula is C10H11NO, 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: Preparation of 2-(3-Hydroxy-4-methylphenyl)acetonitrile: To a stirred solution of 2-(3-methoxy-4-methylphenyl)acetonitrite (5 g, 31 mmol) in dry CH2Cl2 (20 ml) was added drop wise BBr3 (1M in CH2Cl2, 10.02 g, 40 mmol) at-78C under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0C for 5 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml X 3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: methyl acetate 4:1?CH2Cl2: hex 1:1) to give the title compound as an off 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.

Reference:
Patent; Wellstat Therapeutics Corporation; O’NEIL, James, Dennen; SHARMA, Shalini; ARUDCHANDRAN, Ramachandran; EP2282736; (2015); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 64829-31-8, name is 3-Methoxy-4-methylphenylacetonitrile, molecular formula is C10H11NO, 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. Formula: C10H11NO

A 40 mL scintillation vial was charged with compound 79 (250 mg, 1.55 mmol), NBS (331 mg, 1.86 mmol), AIBN (50.9 mg, 0.31 mmol) and CCl4 (5 mL). The reaction mixture was stirred at 70 C. for 2 h. After cooling, the reaction mixture was evaporated to dryness. Flash chromatography (24 g column, 0 to 40% EtOAc in hexanes) gave compound 80 (189 mg, 0.787 mmol, 51% yield) as a solid. LC-MS (ES, m/z): No ion detected. 1H NMR (400 MHz, CDCl3) delta 7.33 (d, J=7.7 Hz, 1H), 6.88 (d, J=7.7 Hz, 1H), 6.84 (s, 1H), 4.53 (s, 2H), 3.92 (s, 3H), 3.74 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64829-31-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; POUDEL, Yam B.; GANGWAR, Sanjeev; HE, Liqi; SIVAPRAKASAM, Prasanna; BROEKEMA, Matthias; COX, Matthew; TARBY, Christine M.; ZHANG, Qian; (75 pag.)US2020/38403; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts