Methanol → Methyl 4-bromo-2-methylbenzoate

Participants

Reaction Steps

4-bromo-2-methylbenzoic acid (100.04 g, 465 mmol), 500 mL of anhydrous methanol, and 5 mL of concentrated sulfuric acid were stirred at reflux under nitrogen for 24 hr. Cooled to room temperature and concentrated in vacuo. Diluted the residue with 500 mL EtOAc and washed with 200 mL 1 M aqueous NaOH, 200 mL water, and 200 mL brine. Dried the solution over MgSO4 and concentrated in vacuo to obtain methyl 4-bromo-2-methylbenzoate as a clear colorless liquid (100.06 g, 437 mmol). 1H NMR (300 MHz, chloroform-d) ppm 2.59 (s, 3 H) 3.89 (s, 3 H) 7.39 (d, J=8.29 Hz, 1 H) 7.42 (s, 1 H) 7.79 (d, J=8.67 Hz, 1 H).

Provenance & Evidence