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

HRID 1048128Notes

Reaction equation

HRID 1048128 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].[Na+]>CS(C)=O.C(OCC)C>[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

5

Reactant 2

HCID 8929Sodium CyanideHCID 1378803,5-Dichlorobenzyl chloride

Product 1

HCID 126899782-(3,5-Dichlorophenyl)acetonitrileYield 51.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

3,5-Dichlorobenzyl chloride (315.6 mg, 1.615 mmol), 0.2 molar in DMSO, was treated with sodium cyanide (158.2 mg, 3.229 mmol) and allowed to stir at ambient temperature for 24 hours. After 24 hours the reaction mixture was diluted with diethyl ether and partitioned between saturated aqueous sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and concentrated to provide the title compound (155.5 mg, 0.836 mmol, 51.8% yield) as a dark red oil.

Workup

  1. custompartitioned between saturated aqueous sodium chloride
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1bd2ba8aff2a4b319d84e53438f6dffa
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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