2-Chloro-5-(2-oxo-propyl)-benzenesulfonamide → 5-(1-Bromo-2-oxo-propyl)-2-chloro-benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].C1C=C[NH+]=CC=1.[Br:22][Br-]Br>C1COCC1>[Br:22][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:4]=1)[C:9](=[O:11])[CH3:10]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred solution of 2-chloro-5-(2-oxo-propyl)-benzenesulfonamide (33a) (1.4 g, 5.7 mmol) in dry THF (100 ml) at room temperature is treated with polymer supported pyridine hydrobromide perbromide (2.9 g, 5.7 mmol) and left to stir overnight. The reaction mixture is then filtered and the solvent removed in vacuo. The residue is purified by chromatography on silica eluting with 1:4 ethyl acetate-hexane to give the titled compound.
Workup
- waitleft
- filtration