Réaction #1368

Équation de réaction

potassium cyanide

ammonium hydroxide

2-methyl-3,4,6-trifluoroaniline

sulfuric acid

sodium nitrite

→

2-methyl-3,4,6-trifluorobenzonitrile

Rendement 38.2%

Solvants

water

water

Conditions de réaction

Traitement

1. 1
   Températurethe mixture is cooled
2. 2
   ExtractionThe mixture is extracted with dichloromethane
3. 3
   Séchagethe extract is dried over sodium sulfate
4. 4
   Concentrationconcentrated
5. 5
   Autrethe residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4)

Mode opératoire

To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), potassium cyanide (43 g), ammonium hydroxide (60 ml) and water (260 ml) at 10°-30° C. The mixture is extracted with dichloromethane and the extract is dried over sodium sulfate, concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4) to give 2-methyl-3,4,6-trifluorobenzonitrile (4.3 g).

Source