2-bromo-1-(2-phenoxyphenyl)ethanone

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of sodium hydride (60% oil dispersion, 0.157 g, 3.92 mmol) and tetrahydrofuran (6.1 mL) was cooled to 0° C., treated dropwise with ethyl 3-oxobutanoate (0.413 mL, 3.27 mmol) and stirred at 0° C. for 30 minutes. A solution of 2-bromo-1-(2-phenoxyphenyl)ethanone (1.05 g, 3.6 mmol) in tetrahydrofuran (2 mL) was added dropwise and stirring was continued for 5.5 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution and washed with saturated aqueous sodium chloride. The combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 2-20% ethyl acetate in hexanes) to give 1.1 g (100%) of the title compound. stirring was continued for 5.5 hours The reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution washed with saturated aqueous sodium chloride The combined aqueous layers were extracted with ethyl acetate The combined organic layers were dried over anhydrous magnesium sulfate filtered concentrated The residue was purified by flash chromatography (silica gel, 2-20% ethyl acetate in hexanes)