Acetyl chloride → 1-(5-Chloro-4-fluoro-2-hydroxyphenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

To 4-chloro-3-fluorophenol (Oakwood #004459, 5.1 g, 35 mmol) was added acetyl chloride (3.6 mL, 51 mmol) and the resulting mixture was heated at 60° C. for 2 hours. Aluminum trichloride (7.0 g, 52 mmol) was added and the mixture was heated at 180° C. for 30 minutes. The reaction mixture was then cooled to room temperature and slowly quenched with 1M HCl while cooling in an ice-bath and stirred for 30 minutes. The precipitate was washed well with water and dried under vacuum to give the desired product (quantitative). This material was used without further purification. 1H NMR (300 MHz, CDCl3): δ 12.41 (s, 1H), 7.80 (m, 1H), 6.79 (m, 1H), 2.60 (s, 3H).

Provenance & Evidence