1. Acetyl chloride (61.7 mL, 867 mmol) was added dropwise to a solution of 3-bromophenol (150 g, 867 mmol) and pyridine (70.0 mL, 867 mmol) in dichloromethane (1000 mL) in an ice bath over a controlled time period of 1 hour. After the dropwise addition, the reaction mixture was stirred at room temperature for 18 hours.
2. After completion of the reaction, water (500 mL) was added to the reaction mixture for dilution and the organic layer was separated. The aqueous layer was extracted with dichloromethane (4 x 150 mL) and the organic layers were combined.
3. The combined organic layers were washed sequentially with 2.5N NaHSO4 (3×150mL), 3N NaOH (3×150mL), water (2×200mL) and brine (2×200mL).
4. The washed organic layer was dried over anhydrous Na2SO4, filtered and the solvent was evaporated to give phenyl 3-bromoacetate as a pink liquid (36.0 g, 86% yield).
5. The product was characterized by GC/MS and 1H NMR: GC/MS data: m/z 214 (M)+ (C8H7BrO2 calculated value 215.04). 1H NMR (DMSO-d6) δ: 7.44-7.48 (ddd, 1H, J1=1.0Hz, J2=2.0Hz, J3=8.1Hz, Ar-H), 7.43 (t, 1H, J1=1.0Hz, J2=2.0Hz, Ar-H). (t, 1H, J=2.1Hz, Ar-H), 7.38 (t, 1H, J=8.1Hz, Ar-H), 7.14-7.18 (ddd, 1H, J1=1.0Hz, J2=2.2Hz, J3=8.1Hz, Ar-H), 2.26 (s, 3H, CH3).
