Reaction #64482

Reaction equation

sodium cyanide

4,4,4-trifluorobutyl bromide

→

title compound

Yield 97.0%

5,5,5,-Trifluorovaleronitrile

Yield 97.0%

Solvents

DMSO

Conditions

Workup

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   OtherThe mixture was then removed from the oil bath
3. 3
   TemperatureThe mixture was heated to 110° C. for about 30 minutes
4. 4
   Temperaturecooled to room temperature
5. 5
   OtherThe mixture was partitioned between H2O and ether
6. 6
   Extractionthe aqueous layer was extracted with an additonal 2 portions of ether
7. 7
   WashThe combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine
8. 8
   DryingThe ether phase was dried over anhydrous Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated

Procedure

A mixture of 882 mg (18 mmole) of sodium cyanide and 9 mL of DMSO was heated in an oil bath at 80° C. for 10 minutes until most of the solid had dissolved. The mixture was then removed from the oil bath and treated with 2.87 g (15 mmole) of 4,4,4-trifluorobutyl bromide. The mixture was heated to 110° C. for about 30 minutes and then cooled to room temperature. The mixture was partitioned between H2O and ether, and the aqueous layer was extracted with an additonal 2 portions of ether. The combined organic fractions were washed successively with 2N HCl (twice), H2O (twice), and brine. The ether phase was dried over anhydrous Na2SO4, filtered, and concentrated to yield 1.99 g (97%) of the title compound as a colorless liquid, suitable for use without further purification; IR (neat) νCO 2260 cm-1.

Source