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

Temperature

60 °C

To 4-chloro-3-fluorophenol (20 g, 100 mmol, from Aldrich) was added acetyl chloride (14.1 mL, 199 mmol) under N2 with stirring. The resulting mixture turned into a clear solution at room temperature and was heated at 60° C. for 2 hours. To the resultant mixture was added aluminum trichloride (25.0 g, 187 mmol) in portions and the mixture was heated at 180° C. for 30 minutes. The solids slowly dissolved at high temp. The reaction mixture was then cooled to room temperature while the flask was swirled carefully in order for the solid to form a thin layer inside the flask and then slowly quenched with 1.0 N HCl (300 mL) while cooling in an ice-bath and stirred overnight. The yellow precipitate was washed well with water and dried under vacuum to give the desired product as a yellow solid (23.8 g), which was directly used in the next step without further purification.

1. customturned into a clear solution at room temperature
2. temperaturethe mixture was heated at 180° C. for 30 minutes
3. dissolutionThe solids slowly dissolved at high temp
4. temperatureThe reaction mixture was then cooled to room temperature while the flask
5. customto form a thin layer inside the flask
6. customslowly quenched with 1.0 N HCl (300 mL)
7. temperaturewhile cooling in an ice-bath
8. stirringstirred overnight
9. washThe yellow precipitate was washed well with water
10. customdried under vacuum

ORD record

ord-d300dc3f85af40f09aeafeb1fdc77a5b

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096600B2