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

HRID 969232Notes

Reaction equation

HRID 969232 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 aqeous layer was extracted with dichloromethane. The combined organic layers were washed with 1N HCl and brine succesively, 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 aqeous layer was extracted with dichloromethane
  3. washThe combined organic layers were washed with 1N HCl and brine succesively
  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-a04b1bc1fcb84fb6ae4dae81877548b3
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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