p-Bromoacetophenone → 1-Bromo-4-(prop-1-en-2-yl)benzene

HRID 543870노트

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HRID 543870 반응식
[Br-].[C:2]1([C:8]([PH3+])([C:15]2C=CC=CC=2)[C:9]2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Br:27]C1C=CC(C(=O)C)=CC=1>C1COCC1.CCCCCC>[Br:27][C:5]1[CH:6]=[CH:7][C:2]([C:8]([CH3:15])=[CH2:9])=[CH:3][CH:4]=1

참가 물질

6

반응물 3

HCID 7466p-BromoacetophenoneHCID 21951224Triphenylmethyl phosphonium bromideHCID 178418339Butyllithium

생성물 1

HCID 36144101-Bromo-4-(prop-1-en-2-yl)benzene수율 58.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a slurry of triphenylmethylphosphonium bromide (71.4 g, 200 mmole), in 500 ml dry THF at 0° C., were slowly added dropwise 135 ml (200 mmole) 1.44 M n-butyllithium in hexane. The mixture was stirred 30 minutes at 0° C., and a solution of 39.8 g (200 mmole) p-bromoacetophenone, in 100 ml dry THF, was slowly added dropwise. The mixture was allowed to warm slowly to ambient temperature, whereafter stirring was continued overnight. The stirred mixture was next filtered and the solvent removed by careful distillation at atmospheric pressure, the resulting residue was diluted with hexane, filtered, and the hexane removed by distillation. The remaining material was distilled, using a water aspirator vacuum, to produce 23.2 g (58.3% yield) of p-bromo-α-methylstyrene, bp 95°-98° C.

후처리

  1. temperatureto warm slowly to ambient temperature
  2. stirringwhereafter stirring
  3. waitwas continued overnight
  4. filtrationThe stirred mixture was next filtered
  5. customthe solvent removed by careful distillation at atmospheric pressure
  6. additionthe resulting residue was diluted with hexane
  7. filtrationfiltered
  8. customthe hexane removed by distillation
  9. distillationThe remaining material was distilled

출처 및 근거

ORD 기록
ord-2fd29c4ecfc743fc98fae64721d15d67
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04447542

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