1-Bromo-2-Chloroethane → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrile

HRID 557969Notes

Reaction equation

HRID 557969 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 14751282-(6-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 221593571-(6-Chloropyridin-3-yl)cyclopropane-1-carbonitrileYield 26.7%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred mixture of the (6-chloropyridin-3-yl)acetonitrile (8.00 g, 0.0524 mol), benzyltriethylammonium chloride (0.8 g, 0.004 mol), and 1-bromo-2-chloro-ethane (8.69 mL, 0.105 mol) was added dropwise sodium hydroxide, 50% aqueous solution (16.1 mL, 0.419 mol) at 50° C. After stirring for 2 h, the reaction mixture was diluted with water and the resulting layers were separated. The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with 1N HCl and brine successively, dried with magnesium sulfate, filtered, and concentrated in-vacuo. The crude product was purified by combiflash to obtain 2.5 g of pure product as a white solid.

Workup

  1. customthe resulting layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with 1N HCl and brine successively
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customThe crude product was purified by combiflash

Sources & evidence

ORD record
ord-83968dd90be14aa39a0a0fa64d8b040a
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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