Hydrochloric Acid → Ethyl 3-(4-bromophenyl)-3-oxopropanoate

Participants

Reaction Steps

To a mixture of 4-bromoacetophenone (80 g, 0.40 mol), ethanol (1 ml) and diethyl carbonate (350 ml) was added sodium hydride (32 g, 60% in oil) by small portions under ice-cooling and the mixture was stirred at room temperature for 4 hrs. The reaction solution was cooled to 0° C. and 6N hydrochloric acid (200 ml) was added. The mixture was extracted with ethyl acetate (200, 100 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=10:1-5:1) to give the objective substance (108.9 g, quantitative) as an oil.

Provenance & Evidence