Reacción #74834

Ecuación de reacción

3,4-difluorophenacyl bromide

o-ethylbenzoylacetonitrile

2,4-dichlorobenzoylacetonitrile

3,4-dimethylbenzoylacetonitrile

m-ethoxybenzoylacetonitrile

sodium cyanide

3,4-diethoxybenzoylacetonitrile

p-isopropoxybenzoylacetonitrile

2,5-difluorobenzoylacetonitrile

p-isopropylbenzoylacetonitrile

m-isobutylbenzoylacetonitrile

→

3,4-difluorobenzoylacetonitrile

Disolventes

water

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAt that time, the mixture was diluted with 100 ml
2. 2
   Filtraciónof water and filtered through Celite®
3. 3
   OtroAcidification of the filtrate gave a cloudy mixture which
4. 4
   Extracciónwas extracted with methylene chloride
5. 5
   OtroThe organic phase was dried
6. 6
   Filtraciónfiltered through Magnesol®
7. 7
   Otroevaporated
8. 8
   OtroRecrystallization of the residue from carbon tetrachloride
9. 9
   Otroprovides 5.3 g
10. 10
    OtroSimilarly prepared

Procedimiento

A solution of 13.2 g. (0.056 mole) of 3,4-difluorophenacyl bromide was dissolved in 100 ml. of ethanol and cooled to 5° C. in ice. A solution of 7.6 g. (0.16 mole) of sodium cyanide in 40 ml. of water was added dropwise over 0.5 hr. and the reaction is stirred for an additional one hour. At that time, the mixture was diluted with 100 ml. of water and filtered through Celite®. Acidification of the filtrate gave a cloudy mixture which was extracted with methylene chloride. The organic phase was dried, filtered through Magnesol® and evaporated. Recrystallization of the residue from carbon tetrachloride provides 5.3 g. (52%) of colorless solid, m.p. 74°-75° C. Similarly prepared were 2,4-dichlorobenzoylacetonitrile, o-ethylbenzoylacetonitrile, p-isopropylbenzoylacetonitrile, m-isobutylbenzoylacetonitrile, 3,4-dimethylbenzoylacetonitrile, m-ethoxybenzoylacetonitrile, p-isopropoxybenzoylacetonitrile, 3,4-diethoxybenzoylacetonitrile, and 2,5-difluorobenzoylacetonitrile.

Fuente