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

Participants

Reaction Steps

4-bromobenzoic acid (17-a, 10 g, 0.05 mol) was dissolved in SOCl2 (100 ml) and the resulting mixture was stirred at rt for 3 hours, then concentrated under vacuum. The residue was dissolved in 1-fluorobenzene (24 g, 0.25 mol) and AlCl3 (8.24 g, 0.06 mol) was added portion-wise with stirring under N2. The resulting reaction mixture was refluxed overnight. The reaction mixture was cooled to temperature and poured into 20% HCl (1500 ml), stirred for 1 h, and the layers were separated. The aqueous layer was further extracted with DCM (2×50 ml). The combined organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was washed with hexane to afford the product, 17-b, (12.2 g, 85%).

Provenance & Evidence