Sodium Cyanide → 3,4-Difluorobenzoylacetonitrile

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.

1. additionAt that time, the mixture was diluted with 100 ml
2. filtrationof water and filtered through Celite®
3. customAcidification of the filtrate gave a cloudy mixture which
4. extractionwas extracted with methylene chloride
5. customThe organic phase was dried
6. filtrationfiltered through Magnesol®
7. customevaporated
8. customRecrystallization of the residue from carbon tetrachloride
9. customprovides 5.3 g
10. customSimilarly prepared

ORD record

ord-46c5ea2bab6c41c3b7fdd1b63e77ae47

Source dataset

uspto-grants-1979_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04173650