Sulfuric Acid → 2,6-Difluoro-3-sulfino-benzoic acid

HRID 2251188Notes

Reaction equation

HRID 2251188 reaction equation
Cl[S:2]([C:5]1[C:6]([F:15])=[C:7]([C:11]([F:14])=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].S([O-])([O-])=O.[Na+].[Na+].S(=O)(=O)(O)O>O>[F:15][C:6]1[C:5]([S:2]([OH:4])=[O:3])=[CH:13][CH:12]=[C:11]([F:14])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 33047963-(Chlorosulfonyl)-2,6-difluorobenzoic acid

Product 1

HCID 690401022,6-Difluoro-3-sulfino-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

41 mmol of 3-chlorosulfonyl-2,6-difluoro-benzoic acid was slowly added over 20 min. to a solution of 310 mmol sodium sulfite in 200 ml of water. The resulting mixture was stirred for one hour at room temperature, cooled to 0° C. and acidified with 20% aqueous sulfuric acid. The sulfinic acid was extracted with ethyl acetate, dried over MgSO4 and concentrated to yield the title compound as a colorless solid. MS (m/e): 220.9 (M−H, 100%)

Workup

  1. temperaturecooled to 0° C.
  2. extractionThe sulfinic acid was extracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da1ee472a81746518e9447cb2640af44
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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