Acetic Acid → (3-Bromo-2,5-dimethoxy-phenyl)-acetic acid

Participants

Reaction Steps

A solution of (3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile 54 (5.2 g, 20.4 mmol) in water (10 ml), conc H2SO4 (10 ml), and AcOH (30 ml) was heated to 100° C. After 3 hr the reaction was cooled and poured into water. The aqueous layer was extracted with EtOAc which was then dried over MgSO4, filtered and concentrated. The product was purified by column chromatography on silica gel (50% EtOAc/Hex) to give a solid (2.8 g, 55%): Mp=62-65° C.; 1H NMR (DMSO-d6) δ 12.45 (br s, 1 H), 7.09 (d, 1 H, J=2.9 Hz), 6.87 (d, 1 H, J=3.0 Hz), 3.72 (s, 3 H), 3.66 (s, 3 H), 3.59 (s, 2 H); MS 273/275 (M−H)−.

Provenance & Evidence