Реакция #64482

Уравнение реакции

sodium cyanide

4,4,4-trifluorobutyl bromide

→

title compound

Выход 97.0%

5,5,5,-Trifluorovaleronitrile

Выход 97.0%

Растворители

DMSO

Условия реакции

Обработка

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

Методика

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.

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