2-Bromophenol (1.16 mL, 10.0 mmol) was dissolved in carbon disulfide (10 mL) and stirred under cooling in an ice-salt bath. Subsequently, anhydrous aluminum chloride (2.7 g, 20.0 mmol) was added in batches, followed by slow dropwise addition of acetyl chloride (0.754 mL, 11.0 mmol). The reaction mixture was maintained under stirring conditions for 1 hour and then refluxed overnight. Upon completion of the reaction, the mixture was quenched by adding a mixture of 1 M hydrochloric acid and ice to the mixture. The mixture was extracted using dichloromethane (3 times) and after combining the organic phases, it was dried and concentrated with anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (eluent: 20% ethyl acetate/hexane to 40% ethyl acetate/hexane gradient elution) to afford the target product 3-bromo-4-hydroxyacetophenone (2.28 g, 53% yield).
