2-(4-Fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile → 2-(4-Fluoro-phenyl)-1-(6-trifluoromethyl-pyridin-2-yl)-ethanone

HRID 8226

Reaktionsgleichung

Reaktionsgleichung von HRID 8226
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=2)C#N)=[CH:4][CH:3]=1>Br>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]=2)=[O:22])=[CH:6][CH:7]=1

Komponenten

3

Edukt 1

HCID 219926412-(4-Fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile

Produkt 1

HCID 219928752-(4-Fluoro-phenyl)-1-(6-trifluoromethyl-pyridin-2-yl)-ethanoneAusbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 260Hydrogen BromideLösungsmittel

Versuchsvorschrift

A slurry of 2-(4-fluoro-phenyl)-3-oxo-3-(6-tri fluoromethyl-pyridin-2-yl)-propionitrile (1.4 g, 4.4 mmol) in 48% HBr is warmed to reflux for 8 h, allowed to stand at ambient temperature 16 h, then warmed at reflux for 8 h. The mixture is extracted with ether, treated with a small amount of sodium bicarbonate, extracted with ether, made basic with solid sodium hydroxide, and extracted again with ether. Ethereal extracts are combined, dried over magnesium sulfate, and concentrated in vacuo to a dark oil. The residual oil is purified on a silica gel cartridge prepared with hexane then eluted with methylene chloride to yield 816 mg (65%) of the title compound as a dark oil.

Aufarbeitung

  1. temperatureto reflux for 8 h
  2. temperaturewarmed
  3. temperatureat reflux for 8 h
  4. extractionThe mixture is extracted with ether
  5. additiontreated with a small amount of sodium bicarbonate
  6. extractionextracted with ether
  7. extractionextracted again with ether
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo to a dark oil
  10. customThe residual oil is purified on a silica gel cartridge
  11. customprepared with hexane
  12. washthen eluted with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-d6f40288404e4a31815604afe24316b9
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087626B2

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