Water → 1,2,4-Trifluoro-5-(methylsulfonyl)benzene

HRID 2251184Notes

Reaction equation

HRID 2251184 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[S:10]([OH:12])=[O:11].[C:13](=O)([O-])[O-].[K+].[K+].CI.O>CN(C=O)C>[F:9][C:5]1[CH:4]=[C:3]([S:10]([CH3:13])(=[O:12])=[O:11])[C:2]([F:1])=[CH:7][C:6]=1[F:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 572413752,4,5-Trifluorobenzenesulfinic acid

Product 1

HCID 467393961,2,4-Trifluoro-5-(methylsulfonyl)benzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,4,5-trifluoro-benzenesulfinic acid (2.0 g) in DMF (17 mL) was added 4.3 g of potassium carbonate, and the reaction mixture was stirred for 5 minutes before methyl iodide (2.2 mL) was added. The reaction mixture was then stirred at room temperature for 60 hours. After such time, water (30 mL) was poured onto the reaction mixture, and the reaction mixture was extracted with diethylether several times. The combined organic phases were dried with sodium sulfate, and the remaining mixture was distilled to yield the title compound as a light yellow oil (2.1 g).

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with diethylether several times
  3. dry with materialThe combined organic phases were dried with sodium sulfate
  4. distillationthe remaining mixture was distilled

Sources & evidence

ORD record
ord-03f9d66dc591461693751a7b38da6516
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

Loading…