Chloroacetonitrile → 2-(4-Fluorophenoxy)acetonitrile

HRID 986915

反応式

HRID 986915 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]#[N:12].C(=O)([O-])[O-].[K+].[K+]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 7856ChloroacetonitrileHCID 97324-FluorophenolHCID 11430Potassium Carbonate

生成物 1

HCID 27830582-(4-Fluorophenoxy)acetonitrile収率 84%

実験手順

A mixture of 4-fluorophenol (22.4 g, 200 mmol), chloroacetonitrile (17.1 g, 220 mmol) and excess powdered potassium carbonate was refluxed for 7 h then the mixture was concentrated under reduced pressure. The residue was mixed with H2O and was extracted with Et2O. The combined organic layers were dried, filtered and concentrated under reduced pressure. The residue was Kugelrohr distilled to provide 2-(4-Fluorophenoxy)acetonitrile (25 g, 84%). The 2-(4-Fluorophenoxy)acetonitrile (25 g, 185 mmol) was reduced with alane [generated from lithium aluminum hydride (19.6 g, 516 mmol) and sulfuric acid (25.3 g, 258 mmol) according to the procedure in Example 1]. The crude product was purified by Kugelrohr distillation to provide the titled compound (12 g).

後処理

  1. temperaturewas refluxed for 7 h
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionThe residue was mixed with H2O
  4. extractionwas extracted with Et2O
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. distillationdistilled

出典と根拠

ORDレコード
ord-620bb07ad593457b905560cdc8f3a2c0
出典データセット
uspto-grants-2003_10
特許番号
US06630469B2

関連ノート

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