Water → 4-(Allyloxy)benzonitrile

HRID 734404노트

반응식

HRID 734404 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 2579494-(Allyloxy)benzonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6d9238e3155b49b6a73e40ea1044b37e
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592361B2

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