Potassium Cyanide → 4-(Trifluoromethyl)phenylacetonitrile

HRID 54274Notes

Reaction equation

HRID 54274 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Br)=[CH:5][CH:4]=1.[C-:13]#[N:14].[K+]>C(O)C.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:13]#[N:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 753594-(Trifluoromethyl)phenylacetonitrileYield 101.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of 250.0 grams (1.05 moles) of 4-trifluoromethylphenylmethyl bromide in 1000 mL of ethanol was heated to about 80° C., and a solution of 109.0 grams (1.67 moles) of potassium cyanide in about 275 mL of water was added. Upon completion of addition, the reaction mixture was stirred at 80° C. for about 1.75 hours. After this time the reaction mixture was cooled to ambient temperature and extracted with three portions of diethyl ether. The combined extracts were washed with two portions of water and one portion of an aqueous solution saturated with sodium chloride. The organic layer was added with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding about 197 grams of 4-trifluoromethylphenylacetonitrile.

Workup

  1. additionUpon completion of addition
  2. temperatureAfter this time the reaction mixture was cooled to ambient temperature
  3. extractionextracted with three portions of diethyl ether
  4. washThe combined extracts were washed with two portions of water and one portion of an aqueous solution saturated with sodium chloride
  5. additionThe organic layer was added with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5f4e3a2d05c4490fa91de08987a504ef
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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