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

HRID 2251223Notes

Reaction equation

HRID 2251223 reaction equation
S([O-])([O-])=O.[Na+].[Na+].Cl[S:8]([C:11]1[C:12]([F:21])=[C:13]([C:17]([F:20])=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])(=[O:10])=[O:9].S(=O)(=O)(O)O>O>[F:21][C:12]1[C:11]([S:8]([OH:10])=[O:9])=[CH:19][CH:18]=[C:17]([F:20])[C:13]=1[C:14]([OH:16])=[O:15]

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

240 mmol of sodium sulfite were dissolved in 150 ml of water. 32 mmol of 3-Chlorosulfonyl-2,6-difluoro-benzoic acid was added under stirring over a period of about 20 min. After stirring for an additional hour at room temperature, the mixture was chilled and acidified with 20% aqueous sulfuric acid. The product was extracted with ethyl acetate to yield the title compound as a colorless solid. MS (m/e): 221.3 (M−H, 34%)

Workup

  1. stirringAfter stirring for an additional hour at room temperature
  2. temperaturethe mixture was chilled
  3. extractionThe product was extracted with ethyl acetate

Sources & evidence

ORD record
ord-ec5e7deb0fc04a268c177cfb642c97ae
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

Loading…