Acetonitrile → 2-chlorobenzoyl cyanide

HRID 1836080Notes

Reaction equation

HRID 1836080 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:11](#[N:13])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:11]#[N:13]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 691102-Chlorobenzoyl chloride

Product 1

HCID 35349442-chlorobenzoyl cyanideYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Orthochlorobenzoyl chloride (17.5 g, 0.1 mol), cuprous cyanide (11.65 g, 0.13 mol), and acetonitrile (8 mL) were refluxed in toluene (15 mL) for 3 hours, and were cooled to room temperature. Then, insoluble substances were removed through filtration, and the residue was washed with toluene. Solvent in the resulting filtrate was evaporated under reduced pressure, and the residue was distilled to obtain orthochlorophenyloxoacetonitrile (12.3 g, 75% yield).

Workup

  1. customThen, insoluble substances were removed through filtration
  2. washthe residue was washed with toluene
  3. customSolvent in the resulting filtrate was evaporated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-a41790d69ecf486ca0e76c084d6a5e59
Source dataset
uspto-grants-2004_08
Patent number
US06777224B2

Reaction notes

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