Potassium Cyanide → 2-(4-Bromo-2-fluorophenyl)acetonitrile

HRID 400303Notes

Reaction equation

HRID 400303 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[C:4]([F:10])[CH:3]=1.[C-:11]#[N:12].[K+]>CCO.CCOC(C)=O.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:11]#[N:12])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrileYield 84.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzylbromide (44.5 g, 166 mmol) in EtOH (118 mL) was added KCN (13.13 g, 182 mmol) and the mixture was stirred at reflux under an argon atmosphere for 18 h. The mixture was allowed to cool and the solvent was concentrated. The residue thus obtained was dissolved in a mixture of EtOAc and H2O and the two phases were separated. The aqueous phase was extracted with EtOAc and the combined organic phases dried and concentrated to a crude product. Purification by chromatography on silica gel (hexane-EtOAc, 10%) afforded the title compound as a reddish oil (30.0 g, 84%).

Workup

  1. temperatureat reflux under an argon atmosphere for 18 h
  2. temperatureto cool
  3. concentrationthe solvent was concentrated
  4. customThe residue thus obtained
  5. customthe two phases were separated
  6. extractionThe aqueous phase was extracted with EtOAc
  7. customthe combined organic phases dried
  8. concentrationconcentrated to a crude product
  9. customPurification by chromatography on silica gel (hexane-EtOAc, 10%)

Sources & evidence

ORD record
ord-b46f558688e04838a7b1809d6d576c15
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

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