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

HRID 855268노트

반응식

HRID 855268 반응식
[Br-].[C:2]1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Li]CCCC.[CH3:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)=O>CS(C)=O>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([C:27]([CH3:2])=[CH2:26])=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 7466p-BromoacetophenoneHCID 517696Phosphine, triphenyl-, hydrobromideHCID 178418339Butyllithium

생성물 1

HCID 36144101-Bromo-4-(prop-1-en-2-yl)benzene수율 53%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a solution of triphenylphosphonium bromide (17.94 g, 50.24 mmol) in DMSO (10 ml) was added n-BuLi (39.25 ml, 1.6M solution in hexane, 62.80 mmol). The solution was stirred at rt for 1 h and to this was added a solution of 4-bromoacetophenone (10.00 g, 50.24 mmol) in DMSO (4 ml). The reaction mixture was then stirred at rt overnight and then quenched with water and the product was extracted with pentane. The organic layers were combined washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by filtration through a short pad of silica using pentane as eluant to give 1-bromo-4-isopropenylbenzene (5.23 g, 53%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.45 (d, J=9.0 Hz, 2H), 7.32 (d, J=9.0 Hz, 2H), 5.36 (m, 1H), 5.10 (m, 1H), 2.12 (m, 3H).

후처리

  1. stirringThe reaction mixture was then stirred at rt overnight
  2. customquenched with water
  3. extractionthe product was extracted with pentane
  4. washThe organic layers were combined washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue which
  9. filtrationwas purified by filtration through a short pad of silica

출처 및 근거

ORD 기록
ord-79570d942cfa40f5aed0615cfbfef6d1
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

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