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

HRID 242098노트

반응식

HRID 242098 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-6575c2c413d944a1a45783584f5dceab
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653100B2

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