Methyl 5-acetyl-2-hydroxybenzoate (1.0 g, 5.1 mmol) was used as starting material, which was dissolved in a mixed CHCl3/EtOAc solvent (40 mL), and copper (II) bromide (2.4 g, 10.8 mmol) was added under stirring. The reaction mixture was gently refluxed at 40-50 °C for 4 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was filtered and subsequently extracted by adding water (50 mL) and EtOAc (40 mL). The EtOAc layer was separated and the aqueous layer was further extracted with EtOAc (20 mL x 2). All EtOAc extracts were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to give the crude product, methyl 5-(2-bromoacetyl)-2-hydroxybenzoate, as a yellow-white solid. The crude product was purified by recrystallization from dichloromethane and hexane to afford the target compound, methyl 5-(2-bromoacetyl)-2-hydroxybenzoate (2), as a white solid (1.2 g, yield about 85%, purity about 95%). The spectral data (1H NMR) of the obtained compound were in agreement with literature reports: 1H NMR (400 MHz, CDCl3) δ (ppm): 11.35 (s, 1H), 8.53 (d, J = 2.3 Hz, 1H), 8.12 (dd, J = 8.8, 2.2 Hz, 1H), 7.08 (d, J = 8.8 Hz, 1H), 4.41 ( s, 2H), 4.02 (s, 3H).
