1,2-Dibromoethane → 1-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

HRID 910879ノート

反応式

HRID 910879 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][C:3]=1[F:11].Br[CH2:13][CH2:14]Br.[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:11]

参加物

7

反応物 3

HCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 116009532-(4-Bromo-3-fluorophenyl)acetonitrile

生成物 1

HCID 117156671-(4-Bromo-3-fluorophenyl)cyclopropane-1-carbonitrile

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of 4-bromo-3-fluorophenylacetonitrile (5 g, 23 mmoles) in toluene (20 ml) is added with 35 mmoles of 1,2-dibromoethane, a 50% NaOH aqueous solution (20 ml) and tetrabutylammonium bromide (1.6 g, 5 mmoles). The mixture is kept under stirring at room temperature for 5-12 hours, then diluted with water and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give a brown solid, which is subjected to chromatography on a silica gel column (200 g), eluting with hexane-ethyl ether 1-1, to afford the product in the solid form.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with 1N HCl
  3. dry with materialwith brine, finally dried
  4. concentrationconcentrated under vacuum
  5. customto give a brown solid, which
  6. washeluting with hexane-ethyl ether 1-1
  7. customto afford the product in the solid form

出典と根拠

ORDレコード
ord-5812937b96094cd88bc431191e21a3d2
出典データセット
uspto-grants-2011_09
特許番号
US08022250B2

反応ノート

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