Potassium Cyanide → 3-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrile

HRID 897162

Reaktionsgleichung

Reaktionsgleichung von HRID 897162
[C-:1]#[N:2].[K+].[Cl:4][C:5]1[C:6](F)=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1.[F-]>O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[Cl:4][C:5]1[C:6]([C:1]#[N:2])=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1

Komponenten

6

Edukt 3

HCID 9032Potassium CyanideHCID 28179Fluoride IonHCID 12680753-Chloro-2-fluoro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 14733743-Chloro-5-(trifluoromethyl)pyridine-2-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of potassium cyanide (71.6 g) in water (215 g) was added during 1 hour to a stirred mixture of 3-chloro-2-fluoro-5-trifluoromethylpyridine (199.5 g) and Aliquat 336 (tricaprylylmethylammonium chloride, 12.1 g) at 30° C. Stirring was maintained at this temperature for 4 hours at which time the amount of starting fluoride was less than 1% by hplc. The lower organic phase was separated and washed with aqueous sodium chloride solution and distilled to give 3-chloro-2-cyano-5-trifluoromethylpyridine (185.8 g, 90% yield) bp 90° C. at 15 mbar. The purity of this product was 98%.

Aufarbeitung

  1. customThe lower organic phase was separated
  2. washwashed with aqueous sodium chloride solution
  3. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-5972c1124d494dfca3add41c53cdbff2
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06921828B2

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