Ammonium Chloride → 6-Fluoro-4-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1880719Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880719
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[N:13])[N:3]=1.[F-:14].[K+].[Cl-].[NH4+]>CS(C)=O>[F:14][C:2]1[N:3]=[C:4]([C:12]#[N:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 595703326-Chloro-4-(trifluoromethyl)pyridine-2-carbonitrile

Produkt 1

HCID 534388006-Fluoro-4-(trifluoromethyl)pyridine-2-carbonitrileAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 9 ml of dimethyl sulfoxide were added 0.9 g of 2-chloro-6-cyano-4-trifluoromethylpyridine, and 0.76 g of potassium fluoride, and the mixture was stirred at 120° C. for 2 hours and 30 minutes. Thereafter, the reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.7 g of 6-fluoro-4-trifluoromethylpyridine-2-carbonitrile.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with tert-butyl=methyl=ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63b0446c35f54cbfbbd828579797f49c
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318776B2

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