Chlorosulfonic acid → 2,4-Difluoro-3-methylbenzenesulfonyl chloride

HRID 337815Notes

Reaction equation

HRID 337815 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH3:9].[S:10]([Cl:14])(=O)(=[O:12])[OH:11]>O>[F:1][C:2]1[C:3]([CH3:9])=[C:4]([F:8])[CH:5]=[CH:6][C:7]=1[S:10]([Cl:14])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 5814931,3-Difluoro-2-methylbenzene

Product 1

HCID 157253752,4-Difluoro-3-methylbenzenesulfonyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1,3-difluoro-2-methylbenzene (5.00 g, 39.0 mmol), chlorosulfuric acid (10.5 mL, 158 mmol) was added with cooling on ice, and the mixture was stirred at room temperature for 5 hours. To the reaction solution, water (100 mL) was added with cooling on ice, followed by extraction with dichloromethane (100 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography to yield the title compound (8.65 g, 98%) as a colorless amorphous solid.

Workup

  1. temperaturewith cooling on ice
  2. temperaturewith cooling on ice
  3. extractionfollowed by extraction with dichloromethane (100 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-897fe641414d4a7faf9fbd47220992ae
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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