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

HRID 705799노트

반응식

HRID 705799 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 534343013-(3-Bromo-4-fluorophenyl)propanenitrile수율 81.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-7bae86022e174a06989fd226a8c83e4e
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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