N,N-Dimethylaniline → Methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate

Participants

Reaction Steps

Aluminium chloride (2.16 g) was added to a stirred solution of methyl 6-(benzenesulfonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 41, 2.15 g) and N,N-dimethylaniline (3.26 g) in DCM (35 mL) and the resultant mixture was stirred for 50 minutes. Ice water and DCM were added and the organic layer was separated, washed with 1M HCl, dried (Na2SO4), filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with DCM to give methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (1.83 g) as a white solid.

Provenance & Evidence