2-Hydroxy-p-toluic acid → 5-bromo-2-hydroxy-4-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

After dissolving 2-hydroxy-4-methylbenzoic acid (24.54 g, 161.29 mmol) in methanol (300 ml), the solution was cooled to −20° C. A solution of bromine (26.03 g) in methanol (50 ml) was added dropwise over 1 hour. The reaction mixture was stirred at room temperature for 1 hour and then concentrated. The residue was heated to dissolution in methanol (100 ml) and water (40 ml) was added. The precipitated crystals were filtered off and washed with 50% methanol-water. The precipitated crystals in the filtrate were also filtered off and washed with 50% methanol-water. The crystals were combined and dried to yield the title compound (24.8 g) as white crystals.

Provenance & Evidence