1-(2-BroMo-6-hydroxyphenyl)ethanone

35065-86-2

55736-69-1

General procedure for the synthesis of 1-(2-bromo-6-hydroxy-phenyl)-ethanone from phenyl 3-bromoacetate: Phenyl 3-bromoacetate (36.0 g, 167 mmol) was mixed with anhydrous AlCl3 (33.5 g, 251 mmol) and heated to 140-150 °C for 2 hours. After the reaction was completed, 100 mL of 5% HCl solution was added to the black solid and the mixture was heated on a boiling water bath until the solid was completely dissolved. After cooling to room temperature, the precipitated brown oil was extracted with CH2Cl2 (3 x 150 mL). The organic layer was separated by adding 300 mL of 5N NaOH solution to the combined organic layers and the precipitate formed dissolved in water. The aqueous phase was acidified with HCl to pH ~2 and extracted with EtOAc (5 x 150 mL). The organic extracts were combined and the solvents were evaporated after drying with Na2SO4 to give 1-(2-bromo-6-hydroxy-phenyl)-acetophenone as beige crystals (35.8 g, 99%).GC/MS data: m/z 214 (M+, calculated value C8H7BrO2 215.05), (calculated mass of a single substance as (M)* 213.96).1H NMR data ( DMSO-d6): δ 11.97 (s, 1H, OH), 7.78 (d, 1H, J = 8.3 Hz, Ar-H), 7.19 (d, 1H, J = 2.0 Hz, Ar-H), 7.13 (dd, 1H, J1 = 8.3 Hz, J2 = 2.0 Hz, Ar-H), 2.60 (s, 3H, CH3).