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

HRID 864328

Reaction equation

HRID 864328 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

HCID 226251752-Methyl-3,4,6-trifluorobenzonitrileYield 38.2%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ba3974c965aa4638a48c1a9eb50065a3
Source dataset
uspto-grants-1996_10
Patent number
US05563138

Linked notes

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