Water → 4-(Allyloxy)benzonitrile

HRID 734404ノート

反応式

HRID 734404 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH:11]=[CH2:10]

参加物

6

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 130194-Cyanophenol

生成物 1

HCID 2579494-(Allyloxy)benzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

4-Hydroxybenzonitrile (30.0 g, 251.8 mmol), allyl bromide (39.6 g, 327.4 mmol), and cesium carbonate (98.5 g, 302.2 mmol) were dissolved in DMF (900 mL), and 1 mL water was added. After stirring for 12 h at ambient temperature, most of the DMF was removed in vacuo. Water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with H2O and brine. The organic layer was dried over Na2SO4, filtered, and the solvent was removed in vacuo. The title compound was obtained as a white crystalline material (40 g, 100%). 1H NMR (400 MHz, CDCl3) δ 4.60 (d, 2H), 5.34 (d, 1H), 5.43 (d, 1H), 6.03 (m, 1H), 6.96 (d, 2H), 7.58 (d, 2H).

後処理

  1. customwas removed in vacuo
  2. additionWater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe combined organic layers were washed with H2O and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-6d9238e3155b49b6a73e40ea1044b37e
出典データセット
uspto-grants-2009_09
特許番号
US07592361B2

反応ノート

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