1,3-Dibromopropane → 1-(6-chloro-2-pyridinyl)-cyclobutanecarbonitrile

HRID 242098ノート

反応式

HRID 242098 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]#[N:10])[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:14][CH2:15][CH2:16]Br>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][CH2:14]2)[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 80011,3-DibromopropaneHCID 14798Sodium HydroxideHCID 17750142(6-Chloropyridin-2-yl)acetonitrile

生成物 1

HCID 582462291-(6-chloro-2-pyridinyl)-cyclobutanecarbonitrile

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-(6-Chloropyridin-2-yl)acetonitrile (5.7 g, 37.4 mmol) was dissolved in dichloromethane (25 ml). 50% aqueous sodium hydroxide solution (26.5 mL) was added dropwise. Benzyltriethylammonium chloride (0.17 g, 0.747 mmol) was added. 1,3-Dibromopropane (7.54 g, 37.4 mmol) were added dropwise and the reaction mixture was stirred over night at room temperature. The reaction mixture was diluted with dichloromethane and washed with water (3×). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica, dichloromethane, methanol). Yield: 2.4 g (10.9 mmol, 29%).

後処理

  1. washwashed with water (3×)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (silica, dichloromethane, methanol)

出典と根拠

ORDレコード
ord-6575c2c413d944a1a45783584f5dceab
出典データセット
uspto-grants-2014_02
特許番号
US08653100B2

反応ノート

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