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

HRID 486253

Reaction equation

HRID 486253 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-172b209286be4041a5e4c1352350b728
Source dataset
uspto-grants-1994_03
Patent number
US05290934

Linked notes

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