Potassium Cyanide → 2-(3,5-Dichlorophenyl)acetonitrile

HRID 1081586Notes

Reaction equation

HRID 1081586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5]Cl.[C-:11]#[N:12].[K+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][C:11]#[N:12])[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 1378803,5-Dichlorobenzyl chloride

Product 1

HCID 126899782-(3,5-Dichlorophenyl)acetonitrile

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a vigorously stirred solution of 3,5-dichlorobenzylchloride (28 g) in dichloromethane (150 ml) was added a mixture of KCN (27.5 g) and tetrabutylammonium hydrogen sulphate (2.38 g) in water (110 ml). After stirring at room temperature for 22 hours, the mixture was diluted with dichloromethane, the organic phase washed with water and concentrated in vacuo to leave an oil.

Workup

  1. washthe organic phase washed with water
  2. concentrationconcentrated in vacuo
  3. customto leave an oil

Sources & evidence

ORD record
ord-d42f2d8ec5c847988a4cc532723360cf
Source dataset
uspto-grants-1996_12
Patent number
US05587380

Reaction notes

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