Hydrochloric Acid → 2-(4-Methoxybenzoyl)-3-phenylbenzothiophene

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry of aluminum chloride (14.6 g, 110 mmol) in 1,2-dichloroethane at 0° C. was added 4-methoxybenzoylchloride (18.7 g, 110 mmol). The mixture was stirred at 0° C. for ten minutes, and 3-phenylbenzo[b]thiophene (21.0 g, 100 mmol) in 1,2-dichlororethane was added. The mixture was stirred for two hours, with the temperature maintained at 0° C. The reaction mixture was poured into a mixture of ice and hydrochloric acid. The resulting mixture was extracted with ether. The ether extract was washed with water, aqueous sodium bicarbonate, and then again with water. The ether layer was dried over magnesium sulfate and evaporated to dryness. The residue was dissolved in ethanol and kept at 5° C. for three days. The product crystallized out, yielding 23.7 g of the title compound. mp: 94° C.-95° C. EA calculated for C22H16O2S: C, 76.72; H, 4.68; O, 9.29. Found: C, 76.54; H, 4.74; O, 9.25.

Provenance & Evidence