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

HRID 846370Notes

Reaction equation

HRID 846370 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. Filtration through silica with toluene followed by concentration then trituration with hexane gave the desired product as a colourless solid. 15.8 g, mp. 31°-32° C.

Workup

  1. washthe organic phase washed with water
  2. concentrationconcentrated in vacuo
  3. customto leave an oil
  4. filtrationFiltration through silica with toluene
  5. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-cdf0d4a7a0f14f69b4c05d0ee748ec75
Source dataset
uspto-grants-1992_08
Patent number
US05136080

Reaction notes

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