Hydrogen Bromide → Bromo-4'-chloro-3'-sulfamoylacetophenone

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[Br:15]Br.Br>C(OCC)(=O)C>[Br:15][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([S:11](=[O:13])(=[O:14])[NH2:12])[CH:4]=1)=[O:10]

Participants

Procedure

4.7 g. of 4'-chloro-3'-sulfamoylacetophenone were suspended in 50 ml of ethyl acetate and to that suspension, some drops of a solution of 3.2 g of bromine were added until the mixture was distinctly brown. The suspension was heated to about 60° - 70° C until the color changed (addition of a drop of 48% hydrobromic acid possible), cooled and the residual amount of the bromine solution was added dropwise at room temperature, while stirring. After distilling off the solvent, 2-bromo-4'-chloro-3'-sulfamoylacetophenone was obtained which melted at 169° C (from n-butanol).