Sodium Hydroxide → 3-Bromo-5-hydroxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo-benzoic acid (20 g, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol). The reaction mixture was heated at 100° C. for 24 h. After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through Celite™. The filtrate was then acidified with 10% aq. HCl and extracted into ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid (12.3 g, 93% yield). HR-ES (−) calcd for C7HSO3Br [M−H]− 214.9349, observed 214.9350

Provenance & Evidence