Hydrochloric Acid → 1-(2'-Fluoro[1,1'-biphenyl]-4-yl)ethanone

Participants

Reaction Steps

A solution of 200 g of 2-fluorobiphenyl in 1500 ml of carbon disulfide was cooled to 0°-5°C and successively treated with 200 g of aluminum chloride over a period of 140 minutes and 113 g of acetyl chloride over a period of 165 minutes. The resulting mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture then was poured carefully into a mixture of ice and aqueous hydrochloric acid. Organic materials were extracted from the resulting acidic mixture with a mixture of diethyl ether and ethyl acetate. The organic extract was washed successively with water, ten percent aqueous sodium hydroxide, and water, and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure and the solid residue was recrystallized from hexane to give 4'-(2-fluorophenyl)-acetophenone. Recrystallization of the material from hexane gave two crops of crystals having the following elemental analyses:

Provenance & Evidence