Acetyl chloride → 2'-Fluoro-4'-hydroxyacetophenone

Participants

Reaction Steps

To a stirred suspension of aluminum chloride (41.6 g, 312 mmol) in 1,2-dichloroethane (100 ml) was added 3-fluorophenol (30.95 g, 276 mmol) dropwise at 0° C. Acetyl chloride (24.0 g, 306 mmol) was added dropwise, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with hexane to give the title compound (3.57 g, 8% yield). 1H-NMR (CDCl3) δ: 7.88-7.82 (m, 1H), 6.74 (dd, J=92 Hz, 1H), 6.64 (dd, J=13, 2 Hz, 1H), 2.62 (d, J=5 Hz, 3H).

Provenance & Evidence