Benzene → 4-Bromobutyryl chloride

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A suspension solution of 3.9 g of benzene (50 mmol) and 1.33 g of aluminum chloride (10 mmol) was cooled to 10°C., and 1.95 g of 4-bromobutyryl chloride (purity: 95%, 10 mmol) was dropwise added to the above solution at the same temperature. After raising the temperature to 20 C. and stirring the mixture for two hours, the solution was added into a 10% aqueous solution of hydrochloric acid that had been cooled to 10° C. Then, after the aqueous phase was extracted with benzene and the organic phase was washed with diluted hydrochloric acid and brine, the solvent was removed by distillation under reduced pressure to give 4-bromobutyrophenone in a 84.7% yield from 4-bromobutyryl chloride.

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