Water → 4-Iodobenzene-1-sulfonyl fluoride

HRID 2292866Notes

Reaction equation

HRID 2292866 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[F-:13].[K+]>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:13])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 73994-Iodobenzenesulfonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 2327404-Iodobenzene-1-sulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

p-Iodobenzenesulfonyl chloride (593 g, 1.96 mol), prepared as described in Example 1(a) above, is dissolved in 2.5 L of acetone and placed in a 5 L three-neck round-bottom flask fitted with a heating mantle, mechanical stirring and a water-cooled condenser. Potassium fluoride (126 g, 2.17 mol) and about 25 mL of water is added and the reaction is heated at reflux for approximately 5 hours. On cooling, the reaction mass is filtered and the solvent removed to provide a crude solid, which on purification, by distillation under high vacuum, affords p-iodobenzenesulfonyl fluoride as a white solid; yield 504 g (90%).

Workup

  1. customplaced in a 5 L three-neck round-bottom flask
  2. customfitted with a heating mantle
  3. temperaturethe reaction is heated
  4. temperatureat reflux for approximately 5 hours
  5. temperatureOn cooling
  6. filtrationthe reaction mass is filtered
  7. customthe solvent removed
  8. customto provide a crude solid, which
  9. customon purification
  10. distillationby distillation under high vacuum

Sources & evidence

ORD record
ord-c3ff98f5f4524cc59e5cd0fd10fa72a9
Source dataset
uspto-grants-1997_11
Patent number
US05684192

Reaction notes

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