Synthesis
3-Bromo-2-methylbenzoic acid (16 g, 74.4 mmol) and iodomethane (21.2 g, 148.8 mmol) were reacted in DMF (160 mL) in the presence of sodium bicarbonate (12.5 g, 148.8 mmol). The reaction mixture was heated and stirred at 60 °C for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and slowly poured into ice water (400 mL). The aqueous phase was extracted with ethyl acetate (4 x 100 mL) and the organic phases were combined. The organic phase was washed sequentially with water (3 x 100 mL) and saturated saline (100 mL) and then dried with anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give methyl 3-bromo-2-methylbenzoate (17.6 g, 100% yield) as an oil. The product was characterized by 1H NMR (CDCl3): δ 7.70 (t, J = 7.6 Hz, 2H), 7.08 (t, J = 7.9 Hz, 1H), 3.90 (s, 3H), 2.67 (s, 3H).
References
[1] Patent: US2003/96841, 2003, A1
[2] Patent: US2014/179667, 2014, A1. Location in patent: Paragraph 0802; 0803
[3] Patent: WO2008/65199, 2008, A1. Location in patent: Page/Page column 74
