Acetonitrile → 2-chlorobenzoyl cyanide

HRID 1297060Notes

Reaction equation

HRID 1297060 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cu][C:12]#[N:13].C(#N)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](=[O:5])[C:12]#[N:13]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 691102-Chlorobenzoyl chlorideHCID 178418546HCID 178418546, compound

Product 1

HCID 35349442-chlorobenzoyl cyanideYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17.5 g (0.1 mol) 2-chlorobenzoyl chloride, 11.65 g (0.13 mol) copper (I) cyanide, and 8 mL of acetonitrile in 15 mL of 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 12.3 g of 2-chlorophenyloxoacetonitrile (yield=75%).

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-ab8b138ed2db46d88e4c0677dbe3a6d8
Source dataset
uspto-grants-2007_07
Patent number
US07250278B2

Reaction notes

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