Methanol → Methyl 2-bromo-4-methylbenzoate

Participants

Reaction Steps

To a solution of 2-bromo-4-methylbenzoic acid (21.5 g, 100 mmol) in MeOH (250 mL) was added thionyl chloride (10.9 mL, 150 mmol) dropwise and then the reaction mixture was refluxed for 4 h. MeOH was distilled out and water was added. It was extracted with EA and the organic layer was washed with saturated sodium bicarbonate solution, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (20:1) to give methyl 2-bromo-4-methylbenzoate (22.3 g, yield 97%) as colorless oil.

Provenance & Evidence