Methanol → 5-Bromo-2-hydroxy-3-methylbenzoic acid

Participants

Reaction Steps

To a mixture of 2-hydroxy-3-methylbenzoic acid (2.1 g, 13.5 mmol) in acetic acid (30 mL) was added bromine (0.7 mL, 13.7 mmol) slowly over 5 minutes. After 24 h, water was added slowly to the reaction mixture and the reaction stirred for 30 min. The resulting precipitate was collected by filtration and washed several times with water. The product was dried overnight under high vacuum to afford 2.8 g (90%). LC/MS: tR=2.86 min, 229.14 (MH)+. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=4 min., Flow rate=4 mL/min.).

Provenance & Evidence