Hydrochloric Acid → (4-Bromophenyl)(4-fluorophenyl)methanone

Participants

Reaction Conditions

Reaction Steps

4-bromo-4′-fluorobenzophenone was synthesized by the Friedel-Crafts acylation of fluorobenzene with 4-bromobenzoyl chloride. More specifically, fluorobenzene (117 grams, 1.2 mol) and 4-bromobenzoyl chloride (39.8 grams, 0.18 mol) was charged to a 250 milliliter flask equipped with a mechanical stirrer, N2 inlet, and reflux condenser. The mixture was then cooled to 0° C. and anhydrous AlCl3 (27 grams, 0.20 mol) was added. The mixture was stirred for 15 minutes at 23° C. for 16 hours. The resulting slurry was poured into 2 liters of water acidified with HCl. The organics were extracted with methylene chloride and subsequently dried over MgSO4. The slurry was filtered and the methylene chloride was removed under reduced pressure. Recrystallization from ethanol gave 43.4 grams (86 percent yield) of the desired crystalline product.

Provenance & Evidence