4-Fluoro-3-(trifluoromethyl)benzonitrile → 4-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile

HRID 1961427

Reaction equation

HRID 1961427 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][S:15]([O-:17])=[O:16].[Na+]>CS(C)=O.O>[CH3:14][S:15]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11])(=[O:17])=[O:16]

Participants

5

Reactant 2

HCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 2733271Sodium methanesulfinate

Product 1

HCID 459337164-(Methylsulfonyl)-3-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-Fluoro-3-(trifluoromethyl)benzonitrile (400 mg, 2.12 mmol) was suspended together with sodium methanesulfinate (216 mg, 2.12 mmol) in DMSO (2 ml) and stirred at 80° C. for 22 hours. The reaction was then cooled, diluted with 25 ml H2O and filtered. Filtered solids were evaporated from toluene to give 536 mg of the title substance (quant).

Workup

  1. temperatureThe reaction was then cooled
  2. filtrationfiltered
  3. filtrationFiltered solids
  4. customwere evaporated from toluene
  5. customto give 536 mg of the title substance (quant)

Sources & evidence

ORD record
ord-25131b47e8044a0abb5bb5e600f8a7d5
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Linked notes

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