2-Fluorobenzenesulphonyl chloride → 2-Fluorobenzene-1-sulfonyl fluoride

HRID 130359Notes

Reaction equation

HRID 130359 reaction equation
[F-:1].[K+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11]>O1CCOCC1>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([F:1])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 1377612-Fluorobenzenesulphonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 141952602-Fluorobenzene-1-sulfonyl fluorideYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Potassium fluoride (99%) (12 g, 216 mmol) was added to a solution of 2-fluoro-benzenesulfonyl chloride (10 g, 51 mmol) in 1, 4 dioxane (35 mL). The reaction mixture was refluxed for 24 hours, then cooled to room temperature and poured into ice water (200 mL). The ice water was extracted with chloroform (3×50 mL). The combined chloroform layers were dried (MgSO4), filtered, and concentrated to afford 2-fluoro-benzenesulfonyl fluoride (2a) as a colorless oil 6.7 g (74%). (M+H)+=177

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. extractionThe ice water was extracted with chloroform (3×50 mL)
  3. dry with materialThe combined chloroform layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f2d75d0aaf984cd6b05673a64eeb488e
Source dataset
uspto-grants-2008_06
Patent number
US07381739B2

Reaction notes

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