Water → HCID 21483948, compound

Participants

Reaction Steps

Methyl 3,4-dichloro-5-methoxybenzoate (5) (518 mg, 2.34 mmol) was suspended in DCM (10 mL) under a reflux condenser fitted with a CaCl2 drying tube. BBr3 (554 μL, 5.86 mmol) was added and the reaction mixture was stirred at RT for 15 h. The reaction mixture was cautiously poured in to iced water (20 mL) and the mixture stirred for 10 min. The product was extracted with EtOAc (50 mL), then the organic solution was washed with brine (2×50 mL) and dried over MgSO4 and filtered. The solvent was removed in vacuo and the residue purified by silica gel chromatogrpahy (40 g, 0-100% EtOAc in isohexane) to afford 3,4-dichloro-5-hydroxybenzoic acid (6) (260 mg, 51% yield) as a white solid: m/z 205 [M−H]− (ES−).

Provenance & Evidence