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

HRID 855268ノート

反応式

HRID 855268 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-79570d942cfa40f5aed0615cfbfef6d1
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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