4-Bromo-2-methylbenzoic acid → Methyl 4-bromo-2-methylbenzoate

Participants

Reaction Steps

To a cooled (0° C.) solution of 4-bromo-2-methylbenzoic acid (15.1 g, 0.070 mol) in tetrahydrofuran (180 mL) and methanol (45 mL) was slowly added (trimethylsilyl)diazomethane (2.0M in hexanes, 42 mL, 0.084 mol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, at which time it was concentrated in vacuo to afford methyl 4-bromo-2-methylbenzoate (16 g, 100%) as a yellow oil. The residue was taken to the next step without further purification. 1H NMR (400 MHz, CDCl3): 7.78 (d, 1H), 7.42 (s, 1H), 7.38 (d, 1H), 3.88 (s, 3H), 2.58 (s, 3H). MS (EI) for C9H9BrO2: 230 (MH+).

Provenance & Evidence