Sodium Cyanide → 3,4-Difluorobenzoylacetonitrile

HRID 46556

Reaktionsgleichung

Reaktionsgleichung von HRID 46556
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5](=[O:8])[CH2:6]Br.[C-]#N.[Na+].ClC1C=C(Cl)C=CC=1C(C[C:22]#[N:23])=O.C(C1C=CC=CC=1C(CC#N)=O)C.C(C1C=CC(C(CC#N)=O)=CC=1)(C)C.C(C1C=C(C=CC=1)C(CC#N)=O)C(C)C.CC1C=C(C=CC=1C)C(CC#N)=O.C(OC1C=C(C=CC=1)C(CC#N)=O)C.C(OC1C=CC(C(CC#N)=O)=CC=1)(C)C.C(OC1C=C(C=CC=1OCC)C(CC#N)=O)C.FC1C=CC(F)=CC=1C(CC#N)=O>O.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([CH2:6][C:22]#[N:23])=[O:8]

Komponenten

14

Edukt 11

HCID 8929Sodium CyanideHCID 27370322-Bromo-1-(3,4-difluorophenyl)ethan-1-oneHCID 43528863-Oxo-3-(4-(propan-2-yl)phenyl)propanenitrileHCID 125401753-(2,5-Difluorophenyl)-3-oxopropanenitrileHCID 136307283-(2,4-Dichlorophenyl)-3-oxopropanenitrileHCID 20387494m-IsobutylbenzoylacetonitrileHCID 203875023-(3,4-Dimethylphenyl)-3-oxopropanenitrileHCID 203875043-(3-Ethoxyphenyl)-3-oxopropanenitrileHCID 203875073,4-DiethoxybenzoylacetonitrileHCID 203875093-(2-Ethyl-phenyl)-3-oxo-propionitrileHCID 203875144-(1-Methylethoxy)-beta-oxobenzenepropanenitrile

Produkt 1

HCID 27582543,4-Difluorobenzoylacetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-46c5ea2bab6c41c3b7fdd1b63e77ae47
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04173650

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