Methanol → Methyl 3-bromo-5-(methylthio)benzoate

Participants

Reaction Steps

To a stirred mixture of 3-bromo-5-methylsulfanyl-benzoic acid (2.2 g, 8.9 mmol), methylene chloride (100 mL), and DMF (5 drops) at 0° C. was added oxalyl chloride (1.0 mL, 12 mmol). The mixture was slowly warmed to room temperature and stirred at room temperature overnight. Methanol (5.0 mL, 120 mmol) and N,N-diisopropylethylamine (5.0 mL, 29 mmol) were added and the mixture was stirred at room temperature for 3 h and then concentrated. The residue was purified by silica gel column (0-50% EtOAc/hexane) to yield an oil. 1H NMR (400 MHz, CDCl3): δ 7.91 (t, 1H, J=1.6 Hz), 7.81 (t, 1H, J=1.6 Hz), 7.52 (t, 1H, J=1.6 Hz), 3.92 (s, 3H), 2.52 (s, 3H).

Provenance & Evidence