Hydrochloric Acid → Methanone, (4-fluorophenyl)(4-nitrophenyl)-

Participants

Reaction Steps

Aluminum chloride (26.0 g, 195 mmol) was added in portions to a solution of 4-nitrobenzoyl chloride (27.8 g, 150 mL) and 4-fluorobenzene (15.8 g, 165 mmol) in carbon disulfide (100 mL). After 1 hour, the resulting yellow mixture was carefully treated with concentrated hydrochloric acid (60 mL) and stirred for 30 minutes. The mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with dilute sodium hydroxide solution, water and brine, dried (MgSO4), and the solvent removed in vacuo. Crystallization from ethyl ether/hexanes gave 4-(4-fluorobenzoyl)-nitrobenzene (10.6 g, 82%) as a white solid, m.p. 87-88° C.; Analysis for C13H8NO3F: Calc.: C, 63.69; H, 3.26; N, 5.71: Found: C, 63.89; H, 3.28; N, 5.78.

Provenance & Evidence