Sodium Cyanide → m-Chlorophenylacetonitrile

HRID 254809ノート

反応式

HRID 254809 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[C-:10]#[N:11].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:10]#[N:11])[CH:7]=[CH:8][CH:9]=1

参加物

4

反応物 2

HCID 8929Sodium CyanideHCID 698381-(Bromomethyl)-3-chlorobenzene

生成物 1

HCID 73722m-Chlorophenylacetonitrile収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

The experimental procedure was followed by the method of Bruno P. Imbimbo et al [J. Med. Chem. 2005, 48, 5707-7520]. A solution of 3-chlorobenzylbromide (5 g, 24.3 mmol) and sodium cyanide (1.3 g, 26.8 mmol) in ethanol (50 ml) was heated to 80° C. for 2 hours. After resulting solution was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in water and organic layer was extracted with ethyl acetate. The solution was evaporated and crude compound was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to yield 2-(3-chlorophenyl)acetonitrile (3.2 g, 87% yield) as colorless oil.

後処理

  1. customAfter resulting solution
  2. concentrationconcentrated under reduced pressure
  3. extractionorganic layer was extracted with ethyl acetate
  4. customThe solution was evaporated
  5. customcrude compound was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

出典と根拠

ORDレコード
ord-8947ee673ebb41428f9ec878f3d5b2cd
出典データセット
uspto-grants-2011_01
特許番号
US07875647B2

反応ノート

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