478375-40-5

off-white powder

Methanol (1.104 g, 0.035 mol) was slowly added to a solution of 3-bromo-5-methylbenzoic acid (5 g, 0.023 mol) in dichlorosulfoxide (30 mL) at 0 °C. The reaction mixture was warmed to 80 °C and stirred for 2 hours. Upon completion of the reaction, the mixture was cooled to 18 °C and concentrated by rotary evaporation to remove the solvent. The residue was washed with water (20 mL) and subsequently extracted with ethyl acetate (100 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated to afford methyl 3-bromo-5-methylbenzoate (5.3 g, 93.8% yield).LC-MS (mass spectrometry) analysis showed the molecular ion peak of the target product to be 229 [M + 1].

[1] Patent: US2015/197493, 2015, A1. Location in patent: Paragraph 0871; 0872; 0873; 0874
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 16, p. 7358 - 7373
[3] Patent: US2015/225355, 2015, A1. Location in patent: Paragraph 0868; 0869