Реакция #595299

Уравнение реакции

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

Выход 85.0%

Растворители

AcOEt

AcOEt

Условия реакции

Обработка

1. 1
   Температураunder reflux for 3 h
2. 2
   Промывкаwashed with water
3. 3
   Другоеthe combined organic phases were dried
4. 4
   Концентрированиеconcentrated to dryness under reduced pressure
5. 5
   ДругоеPurification by chromatography on silica gel

Методика

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)].

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