18-Crown-6 → 3-Chloro-4-fluorobenzenesulfonyl fluoride
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[F-:13].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([F:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the commercially available 3-chloro-4-fluorobenzenesulfonyl chloride (7 g, 30 mmol) in CH3CN (40 mL) was added KF (7 g, 120 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-12a (4.2 g, 95.5%) as a pale yellow solid. ESI-MS (M+1): 213.2 calc. for C6H3CIF2O2S