Dimethylformamide → 2-Pyridinecarbonitrile, 5-fluoro-4-(trifluoromethyl)-

HRID 1880726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880726
[CH3:1][N:2](C)C=O.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[C:10]([F:17])=[CH:9][N:8]=1>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:17][C:10]1[C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]([C:1]#[N:2])=[N:8][CH:9]=1

Komponenten

6

Edukt 2

HCID 6228DimethylformamideHCID 56604232HCID 56604232, Verbindung

Produkt 1

HCID 595703462-Pyridinecarbonitrile, 5-fluoro-4-(trifluoromethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To 12 ml of N,N-dimethylformamide were added 0.8 g of 2-bromo-5-fluoro-4-trifluoromethylpyridine, 1.41 g of zinc cyanide and 0.28 g of tetrakistriphenylphosphinepalladium, and the mixture was stirred at 95° C. for 14 hours. After allowing to cool, the reaction solution was poured into water, and the resultant solution was extracted with diethyl ether three times, 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 0.5 g of 5-fluoro-4-trifluoromethylpyridine-2-carbonitrile.

Aufarbeitung

  1. temperatureto cool
  2. extractionthe resultant solution was extracted with diethyl 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-f56b6dffddac41eb83ece9753e2dc291
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318776B2

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