Water → 4-(Allyloxy)benzonitrile

HRID 603381ノート

反応式

HRID 603381 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収率 100%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Hydroxybenzonitrile (30.0 g, 252 mmol), allyl bromide (39.6 g, 327 mmol), and Cs2CO3 (98.5 g, 302 mmol) were dissolved in DMF (900 mL), and water (1 mL) was added. After stirring for 12 h at rt, the reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted with EtOAc (2×). The combined organic layers were washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure yielding 40 g (100%) of the title compound as a white crystalline solid. 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. concentrationthe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1b8a9898d51542c2a06f985cce964aa3
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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