Water → 3-(3-Bromo-4-fluorophenyl)propanenitrile

HRID 474554ノート

反応式

HRID 474554 の反応式
[Br:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]#[N:12])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

5

反応物 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 61702072(E)-3-(3-Bromo-4-fluorophenyl)acrylonitrile

生成物 1

HCID 534343013-(3-Bromo-4-fluorophenyl)propanenitrile収率 81.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a solution of (E)-3-(3-bromo-4-fluorophenyl)acrylonitrile (35.0 g, 108 mmol) in ethanol (20 mL) at 0° C. was added sodium tetrahydroborate (16.40 g, 434 mmol). The reaction mixture was allowed to warm to 70° C. and stirred for 4 h. Water was added to quench the reaction, and the organic layer was separated. The water layer was extracted with DCM twice, and the combined organic phase was dried and concentrated. The residue was purified by chromatography to afford the title compound as an oil (20 g, 64.7% yield). LCMS: rt=1.45 min, [M+H+]=228

後処理

  1. customto quench
  2. customthe reaction
  3. customthe organic layer was separated
  4. extractionThe water layer was extracted with DCM twice
  5. customthe combined organic phase was dried
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-38b54ffd07654d4e985484f1b6e74643
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

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