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

HRID 510733Notes

Reaction equation

HRID 510733 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-a4ac14a706724d22abf2d42a616213db
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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