Reaction #595299

Reaction equation

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

Yield 85.0%

Solvents

AcOEt

AcOEt

Conditions

Workup

1. 1
   Temperatureunder reflux for 3 h
2. 2
   Washwashed with water
3. 3
   Otherthe combined organic phases were dried
4. 4
   Concentrationconcentrated to dryness under reduced pressure
5. 5
   OtherPurification by chromatography on silica gel

Procedure

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)].

Source