Methanol → Methyl 4-bromo-2-hydroxybenzoate

Participants

Reaction Steps

A solution of 4-bromo-2-hydroxybenzoic acid (1.0 g) in methanol (10 ml) was treated cautiously with conc. sulphuric acid (0.5 ml) then stirred at 75° under nitrogen for 7 h. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (30 ml) and water (30 ml). The aqueous layer was re-extracted with ethyl acetate (30 ml) and the combined organic extracts were washed with saturated aqueous sodium bicarbonate (2×50 ml) and water (50 ml). The dried (MgSO4) extracts were concentrated under vacuum to give the title compound as a beige solid (0.7 g).

Provenance & Evidence