Sulfuric Acid → 3,4-Difluoro-benzenesulfinic acid

HRID 2251251Notes

Reaction equation

HRID 2251251 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[F:7][C:8]1[CH:9]=[C:10]([S:15](Cl)(=[O:17])=[O:16])[CH:11]=[CH:12][C:13]=1[F:14].[OH-].[Na+].OS(O)(=O)=O>O.O1CCOCC1>[F:7][C:8]1[CH:9]=[C:10]([S:15]([OH:17])=[O:16])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 27369133,4-Difluorobenzene-1-sulfonyl chloride

Product 1

HCID 138368283,4-Difluoro-benzenesulfinic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 2.47 mol sodium sulfite in 1120 ml water at RT was added dropwise over 20 min a solution of 329 mmol 3,4-difluoro-benzenesulfonyl chloride in 560 ml dioxane and stirring continued for a further 30 min. 1 M aq NaOH was then added dropwise until the reaction mixture was pH 14, and the mixture was then allowed to stir at RT for a further 16 h. The mixture was then cooled to 0° C. and concentrated H2SO4 added until the reaction mixture was pH 1. The mixture was extracted three times with ethyl acetate, and the combined organic phases washed with saturated aq NaCl solution and then dried with Na2SO4. Evaporation in vacuo yielded the title compound. MS (m/e): 177.1 ([M−H]−, 100%)

Workup

  1. stirringto stir at RT for a further 16 h
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. washthe combined organic phases washed with saturated aq NaCl solution
  4. dry with materialdried with Na2SO4
  5. customEvaporation in vacuo

Sources & evidence

ORD record
ord-6f9a22890200470c8a87c608791d3db3
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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