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

HRID 705799ノート

反応式

HRID 705799 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-7bae86022e174a06989fd226a8c83e4e
出典データセット
uspto-grants-2015_11
特許番号
US09174968B2

反応ノート

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