1-(3-Bromo-4-fluorophenyl)ethan-1-one → 3'-Cyano-4'-fluoroacetophenone

HRID 2175805Notes

Reaction equation

HRID 2175805 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].[C:12]([Cu])#[N:13]>CN(C=O)C>[C:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([CH:3]=1)[C:12]#[N:13])(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 705081-(3-Bromo-4-fluorophenyl)ethan-1-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 224583893'-Cyano-4'-fluoroacetophenone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(3-bromo-4-fluorophenyl)ethanone (81.3 g, 0.344 mol) in 300 mL of DMF was added CuCN (67.4 g, 0.749 mol) and the mixture was heated to reflux and stirred under N2 for 10 h. The reaction mixture was quenched with water and extracted with ether. The organic layer was washed with brine dried over Na2SO4 and concentrated in vacuum. The residue was purified with silica gel column chromatography to give the product 5-acetyl-2-fluorobenzonitrile.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-5837771eebdb4abb88e20418caeaf46d
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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