m-Bromobenzenesulphonyl chloride → 3-Bromobenzene-1-sulfonyl fluoride

HRID 855511Notes

Reaction equation

HRID 855511 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[F-:12].[K+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([F:12])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 522689Potassium Fluoride

Product 1

HCID 707000393-Bromobenzene-1-sulfonyl fluorideYield 81%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-bromophenylsulfonyl chloride (5 g, 0.0196 mol) in acetonitrile (20 ml) was added potassium fluoride (2.27 g, 0.0391 mol) followed by 18-crown-6 ether (0.08 g) and the reaction stirred at room temperature for 18 h. The reaction mixture was then washed with water (60 ml), extracted with ethyl acetate (3×80 ml) and the combined organic extracts dried (Na2SO4). Solvents were evaporated in vacuo to give a yellow oil (3.79 g, 81%).

Workup

  1. washThe reaction mixture was then washed with water (60 ml)
  2. extractionextracted with ethyl acetate (3×80 ml)
  3. dry with materialthe combined organic extracts dried (Na2SO4)
  4. customSolvents were evaporated in vacuo

Sources & evidence

ORD record
ord-8932e01196e94845afce617abd7cec0d
Source dataset
uspto-grants-2007_08
Patent number
US07262188B2

Reaction notes

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