Acetonitrile → 3-Chlorobenzoyl cyanide

HRID 1297061Notes

Reaction equation

HRID 1297061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[Cu][C:12]#[N:13].C(#N)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 69252Benzoyl chloride, 3-chloro-HCID 178418546HCID 178418546, compound

Product 1

HCID 119842783-Chlorobenzoyl cyanideYield 169.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

43.8 g (0.1 mol) 3-chlorobenzoyl chloride, 29.1 g (0.13 mol) copper (I) cyanide, and 20 mL acetonitrile in 37 mL toluene was refluxed for 3 hours, and then cooled to room temperature. Insoluble material was filtered and the residue was washed with toluene. The solvent in the resulting filtrate was evaporated under reduced pressure, and the residue was distilled to yield 28 g 3-chlorophenyloxoacetonitrile (yield=68%).

Workup

  1. filtrationInsoluble material was filtered
  2. washthe residue was washed with toluene
  3. customThe solvent in the resulting filtrate was evaporated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-277e3dda00e143e4bd1664cf26cbe709
Source dataset
uspto-grants-2007_07
Patent number
US07250278B2

Reaction notes

Loading…