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

HRID 242098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 242098
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6575c2c413d944a1a45783584f5dceab
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653100B2

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