Sodium Cyanide → 2-(Trifluoromethyl)phenylacetonitrile

HRID 1934728Notes

Reaction equation

HRID 1934728 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Br.[C-:13]#[N:14].[Na+]>C(O)C.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][C:13]#[N:14]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 764352-(Trifluoromethyl)phenylacetonitrileYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(trifluoromethyl)benzyl bromide (1.50 g) in ethanol (15 mL) was added a solution of sodium cyanide (461 mg) in water (15 mL) at ambient temperature, and the mixture was heated for 3 hours under reflux . After evaporation of the organic solvent, the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give [2-(trifluoromethyl)phenyl]acetonitrile (1.08 g) as an oil.

Workup

  1. temperaturethe mixture was heated for 3 hours
  2. temperatureunder reflux
  3. customAfter evaporation of the organic solvent
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9c0f7237f1d8445896431d7ac45de7d5
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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