Water → 1-(2-Chlorophenyl)cyclopropanecarbonitrile

HRID 1374628Notes

Reaction equation

HRID 1374628 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].Br[CH2:12][CH:13](Br)C.[H-].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:9]#[N:10])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 65531,2-DibromopropaneHCID 24758Sodium hydrideHCID 76112(o-Chlorophenyl)acetonitrile

Product 1

HCID 103133551-(2-Chlorophenyl)cyclopropanecarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 13.1 g of 2-chlorophenylacetonitrile and 20.3 g of 1,2-dibromopropane in 142 ml of DMF is mixed with 9 g of sodium hydride [55–65% in oil] at room temperature. It is stirred for several hours and carefully added to water. After extraction with ethyl acetate and filtration by silica gel, the desired product is obtained: 13.1 g

Workup

  1. extractionAfter extraction
  2. filtrationwith ethyl acetate and filtration by silica gel

Sources & evidence

ORD record
ord-e765fb82ca28462e87cacf9505a74cd1
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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