p-Bromobenzenesulfonyl chloride → 4-Bromobenzene-1-sulfonyl fluoride

HRID 60416Notes

Reaction equation

HRID 60416 reaction equation
[Br: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+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([F:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 2855718-Crown-6HCID 522689Potassium Fluoride

Product 1

HCID 124097144-Bromobenzene-1-sulfonyl fluoride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-bromobenzenesulfonyl chloride (2.29 g, 9 mmol) in CH3CN (45 mL) was added KF (2.1 g, 36 mmol) and 18-crown-6 (0.5 g), then the mixture was stirred at room temperature overnight. The mixture was quenched with aqueous water and extracted with EtOAc, the organic layer was washed with brine, dried over anhydrous Na2SO4, concentrated to give the crude product which was purified by column to give the reagent R-10a (1.6 g, 74.4%) as a pale yellow solid. ESI-MS (M+1): 239.2 calc. for C6H4BrFO2S.

Workup

  1. customThe mixture was quenched with aqueous water
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c73b0076c50443cea0069ee7dd4455c0
Source dataset
uspto-grants-2016_09
Patent number
US09440989B2

Reaction notes

Loading…