Reaktion #74834

Reaktionsgleichung

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

Lösungsmittel

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAt that time, the mixture was diluted with 100 ml
2. 2
   Filtrationof water and filtered through Celite®
3. 3
   SonstigeAcidification of the filtrate gave a cloudy mixture which
4. 4
   Extraktionwas extracted with methylene chloride
5. 5
   SonstigeThe organic phase was dried
6. 6
   Filtrationfiltered through Magnesol®
7. 7
   Sonstigeevaporated
8. 8
   SonstigeRecrystallization of the residue from carbon tetrachloride
9. 9
   Sonstigeprovides 5.3 g
10. 10
    SonstigeSimilarly prepared

Vorschrift

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.

Quelle