Hydrochloric Acid → 1-(4-Bromo-2-fluorophenyl)-3-chloro-1-propanone

A solution of 4-Bromo-2-fluoro-benzoyl chloride (26.79 g, 113 mmol) in dichloroethane was added to a stirred suspension of aluminum chloride (15 g, 113 mmol)in dichloroethane at room temperature. The suspension turned into a dark solution after adding the acid chloride. The temperature was maintained by an ice-bath. Ethylene gas was bubbled through the reaction mixture for 3 hours until the acid chloride was consumed. The reaction mixture was stirred over night at room temperature. The reaction mixture was cooled to 0° C. and quenched with a 4 M hydrochloric acid solution (34 ml, 134 mmol). The organic phase was separated and the water phase was extracted with dichloromethane. The combined organic phases were washed with water, saturated sodium bicarbonate solution and brine, dried over sodium sulfate and filtered. After concentrating under reduced pressure, crude 1-(4-Bromo-2-fluoro-phenyl)-3-chloro-propan-1-one (27.45 g, 103 mmol) was obtained which was carried over to the next step.

1. temperatureThe temperature was maintained by an ice-bath
2. customEthylene gas was bubbled through the reaction mixture for 3 hours until the acid chloride
3. customwas consumed
4. temperatureThe reaction mixture was cooled to 0° C.
5. customThe organic phase was separated
6. extractionthe water phase was extracted with dichloromethane
7. washThe combined organic phases were washed with water, saturated sodium bicarbonate solution and brine
8. dry with materialdried over sodium sulfate
9. filtrationfiltered
10. concentrationAfter concentrating under reduced pressure

ORD record

ord-2676c8ff17de42808aa29d5bc6dfa330

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299077B2