Methanol → Methyl 3-bromo-4-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask containing 3-bromo-4-chlorobenzoic acid (5.0 g, 21.2 mmol) (commercially available from Aldrich, CAS No. 42860-10-6) was added a cold solution of MeOH (60 mL) and sulfuric acid (1.4 mL). The mixture was heated to 80° C. and monitored with TLC. After 17 hours, the reaction was cooled to room temperature and diluted with water. The aqueous phase was extracted with diethyl ether (3×50 mL), and the combined organic layers were dried over anhydrous magnesium sulfate. After filtration, the organic solvent was removed in vacuo to yield white solid 13.1 (5.0 g, 96% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.28 (1H, d, J=2.0 Hz), 7.93 (1H, m), 7.52 (1H, d, J=8.2 Hz), 3.93 (3H, s).

Provenance & Evidence