Dimethylacetamide → 4-acetyl-3-chlorobenzonitrile

HRID 2391750Notes

Reaction equation

HRID 2391750 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([Cl:11])[CH:3]=1.[CH3:12][N:13](C)C(=O)C>[Zn].[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:12]#[N:13])=[CH:3][C:4]=1[Cl:11])(=[O:10])[CH3:9]

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-one

Product 1

HCID 686137084-acetyl-3-chlorobenzonitrile

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
160 °C

Procedure

A mixture of 59 mg of zinc, 528 mg of zinc cyanide, 2.1 g of 1-(4-bromo-2-chlorophenyl)ethanone and 367 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) in 10 ml N,N-dimethylacetamide is stirred for 4 h at 160° C. The reaction mixture is allowed to cool down to room temperature and stirred for 14 h at room temperature. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (n-hexane/ethyl acetate, 85/15 (v/v)) to yield the title compound.

Workup

  1. temperatureto cool down to room temperature
  2. stirringstirred for 14 h at room temperature
  3. customThe solvent is removed under reduced pressure
  4. customthe resulting residue is purified by flash chromatography (n-hexane/ethyl acetate, 85/15 (v/v))

Sources & evidence

ORD record
ord-4942d6dd5d4141848006671b78b528aa
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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