Sodium Hydroxide → (E)-3-(3-Bromo-4-fluorophenyl)acrylonitrile

HRID 474553ノート

反応式

HRID 474553 の反応式
[Br-].[C:2]([CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[OH-].[Na+].[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH:30]=O>C(Cl)Cl.O>[Br:26][C:27]1[CH:28]=[C:29](/[CH:30]=[CH:4]/[C:2]#[N:3])[CH:32]=[CH:33][C:34]=1[F:35]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 11811037(Cyanomethyl)triphenylphosphonium bromide

生成物 1

HCID 61702072(E)-3-(3-Bromo-4-fluorophenyl)acrylonitrile収率 125.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of (cyanomethyl)triphenylphosphonium bromide (70.6 g, 185 mmol) and sodium hydroxide (7.39 g, 185 mmol) in DCM (100 mL) and water (300.00 mL) at 0° C. was added 3-bromo-4-fluorobenzaldehyde (25.0 g, 123 mmol). It was allowed to warm to room temperature and stirred for 2 h. The organic layer was separated, and the water layer was extracted with DCM twice. The combined organic phases were dried over Na2SO4 and concentrated to give a crude product, which was washed with diethyl ether. The residue was purified to give the title compound as a white solid (35 g, 88% yield). LCMS: rt=1.50 min, [M+H+]=226

後処理

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with DCM twice
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. washwas washed with diethyl ether
  7. customThe residue was purified

出典と根拠

ORDレコード
ord-99c933f36cb64fdb8139b594bd3d64b7
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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