3-Furoic acid → 5-Bromofuran-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of pyridinium tribromide (14.3 g, 44.6 mmoles) in acetic acid (20 ml) was added 3-furoic acid (5 g, 44.6 mmoles). The resulting mixture was heated at 40° C. for 16 hours. The acetic acid was evaporated; the residue was dissolved in dichloromethane (50 ml), washed with water (3×50 ml) and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC (gradient: 20% acetonitrile/80% water containing 0.1% trifluoroacetic acid to 80% acetonitrile/20% water at a rate of 1%/min) to afford 5-Bromo-furan-3-carboxylic acid (7) as a white solid. LC/MS System A; Rt=2.52 mins, m/z (ES−)=189/191 (M−H for C5H3BrO3).

Provenance & Evidence