Potassium Cyanide → 4-(Trifluoromethyl)phenylacetonitrile
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]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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 dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding about 197 grams of 4-trifluoromethylphenylacetonitrile.
Workup
- additionUpon completion of addition
- temperatureAfter this time the reaction mixture was cooled to ambient temperature
- extractionextracted with three portions of diethyl ether
- washThe combined extracts were washed with two portions of water and one portion of an aqueous solution saturated with sodium chloride
- dry with materialThe organic layer was dried with magnesium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b6e1ddc8fd1f4706b5c6e492ae8c5d84
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05502054
Reaction notes
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