Bromine → Methyl 3-bromo-2-hydroxy-6-methylbenzoate

Participants

Reaction Steps

A solution of bromine (16.8 ml) in acetic acid (150 ml) was added dropwise to a stirred and cooled solution of methyl 6-methyl-2-oxocyclohex-3-enecarboxylate (prepared according to Hauser et al, Synthesis 1980 814, 28.2 g) in acetic acid at 0° C. The resultant mixture was stirred and heated at reflux for 24 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with sodium bicarbonate (saturated aqueous solution) and brine, then dried (MgSO4 and activated charcoal) and filtered through Celite. The filtrate was evaporated to dryness to give methyl 3-bromo-2-hydroxy-6-methylbenzoate (30.8 g) as an oil.

Provenance & Evidence