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

HRID 242098Notes

Reaction equation

HRID 242098 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-6575c2c413d944a1a45783584f5dceab
Source dataset
uspto-grants-2014_02
Patent number
US08653100B2

Reaction notes

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