Application of 148547-19-7, 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. 148547-19-7 name is Methyl 4-bromo-3-methylbenzoate, 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.
Step A. (2-Methyl-2′-methoxy-[1,1′-biphenyl]-4-yl)carboxylic acid methyl ester A mixture of 3-methyl-4-bromobenzoic acid methyl ester (2.0 g, 8.7 mmol), 2-methoxyphenyl boronic acid (1.32 g, 8.7 mmol) and sodium carbonate (4.1 g, 38.7 mmol) in toluene:ethanol:water (50 mL:25 mL: 25 mL) was purged with nitrogen for 1 hour. After addition of the tetrakis(triphenylphosphine) palladium(0) catalyst (0.50 g, 0.43 mmol), the reaction mixture was heated at 100 C. overnight. After cooling, the reaction was filtered through Celite and the cake washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a brown oil. Purification by flash chromatography on silica gel with a solvent gradient from 20% to 50% dichloromethane in hexane gave 2.0 g of product as a colorless oil. 1H NMR (DMSO-d6, 400 MHz): delta2.09 (s, 3H), 3.70 (s, 3H), 3.85 (s, 3H), 7.00-7.04 (m, 1H), 7.08-7.11 (m, 2H), 7.23 (d, 1H), 7.37-7.41 (m, 1H), 7.77-7.79 (m, 1H), 7.83-7.84 (m, 1H). MS [(+)APCI, m/z]: 257[M+H]+. Anal. Calcd. for C16H16O3: C, 74.98, H, 6.29. Found: C, 74.06, H, 6.17.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-bromo-3-methylbenzoate, and friends who are interested can also refer to it.
Reference:
Patent; Wyeth; US2003/8863; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics