4-Fluorobenzenesulfonyl chloride → 4-Fluorobenzenesulfonyl fluoride

HRID 60415Notes

Reaction equation

HRID 60415 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F-:12].[K+].C([O-])(O)=O.[Na+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 522689Potassium Fluoride

Product 1

HCID 30819424-Fluorobenzenesulfonyl fluorideYield 102.4%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 4-Fluorobenzenesulfonyl chloride (50 g, 0.256 mol) in ACN (500 mL) was added KF (74.36 g, 5 eq) and 18-crown-6 (2 g) at r.t., then the mixture was stirred at r.t. overnight. The mixture was detected by LC-MS, then saturated aqueous NaHCO3 was added and the mixture was extracted with EtOAc, the organic layer was washed with saturated aqueous NaHCO3, brine, dried over anhydrous Na2SO4, concentrated to give the crude compound 4-Fluorobenzenesulfonyl fluoride (46.70 g) as pale yellow oil which was used for the next step without further purification. ESI-MS (M+1): 179 calc. for C6H4F2O2S.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washthe organic layer was washed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cad535deeb50482a815c092fc9f19b18
Source dataset
uspto-grants-2016_09
Patent number
US09440989B2

Reaction notes

Loading…