3-Hydroxybenzoic Acid → 4-Bromo-3-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-hydroxybenzoic acid 5 (18.2 g, 0.132 mol) in 180 ml of glacial acetic acid cooled in a water bath was slowly added over a period of 2 h bromine (21.1 g, 0.132 mmol) in 70 ml of acetic acid. The solution was stirred overnight. After removing bromine and 160 ml of acetic acid under reduced pressure, the mixture was cooled to 0° C., filtered, washed (50 ml of cold water), and dried under vacuum to give a white solid. Crystallization (H2O) gave 4-bromo-3-hydroxybenzoic acid as white crystals (5.5 g, 19%).

Provenance & Evidence