Sulfuric Acid → 2-Methyl-3,4,6-trifluorobenzonitrile

HRID 1272

Reaktionsgleichung

Reaktionsgleichung von HRID 1272
[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[C-:21]#[N:22].[K+].[OH-].[NH4+]>S([O-])([O-])(=O)=O.[Cu+2].O>[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1[C:21]#[N:22]

Komponenten

8

Edukt 5

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 226251783,4,6-Trifluoro-2-methylanilineHCID 23668193Sodium Nitrite

Produkt 1

HCID 226251752-Methyl-3,4,6-trifluorobenzonitrileAusbeute 38,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturethe mixture is cooled
  2. extractionThe mixture is extracted with dichloromethane
  3. dry with materialthe extract is dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-1e9ca78c8b7943d3b81ed784f0fbf2a2
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723648

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