Sulfuric Acid → HCID 13836828, compound

HRID 2374240Notes

Reaction equation

HRID 2374240 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 13836828HCID 13836828, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To sodium sulfite (22.2 g, 176 mmol) in 80 ml water at RT was added dropwise over 20 min a solution of 3,4-difluoro-benzenesulfonyl chloride (5.00 g, 23.5 mmol) in 40 ml dioxane. 1 M aq NaOH (40 ml) 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 (4.21 g, 97%) as a white crystalline solid. MS (ISN): 177.1 M−H−

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  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-db22e059174e4fde91fea6cd4e23ede4
Source dataset
uspto-grants-2008_12
Patent number
US07462617B2

Reaction notes

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