Reacción #595299

Ecuación de reacción

1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene

N-bromosuccinimide

benzoyl peroxide

→

1-[3-bromo-1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene

Rendimiento 85.0%

Disolventes

AcOEt

AcOEt

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 3 h
2. 2
   Lavadowashed with water
3. 3
   Otrothe combined organic phases were dried
4. 4
   Concentraciónconcentrated to dryness under reduced pressure
5. 5
   OtroPurification by chromatography on silica gel

Procedimiento

A stirred solution of 1-[1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene (680 mg, 2.56 mmol), N-bromosuccinimide (823 mg, 4.62 mmol) and benzoyl peroxide (30 mg) in AcOEt (15 ml) was heated under reflux for 3 h. After cooling to room temperature, the reaction mixture was diluted with AcOEt and washed with water, and the combined organic phases were dried and concentrated to dryness under reduced pressure. Purification by chromatography on silica gel gave 1-[3-bromo-1-(2-chlorophenyl)prop-1-en-2-yl]-2,4-difluorobenzene as a 52/48 mixture of diastereoisomers [colourless oil, 792 mg, yield 85%; GC/MS: m/z=344 (M+); HPLC/MS: log P(HCOOH)=4.80 (major diastereoisomer), 5.25 (minor diastereoisomer)].

Fuente