2,6-Dichlorotoluene → 2,4-Dichloro-3-methylbenzene-1-sulfonyl chloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([Cl:8])[CH:5]=[CH:6][C:7]=1[S:11]([Cl:10])(=[O:13])=[O:12]Participants
3
Procedure
10 ml of chlorosulfonic acid were dropwise added with 4.8 ml of 2,6-dichlorotoluene in two hours, under magnetic stirring at room temperature. After completion of the addition, the mixture was heated at 40° C. for two hours, thereby obtaining a purple solution, which was cooled and carefully poured into ice-water (0.5 l), stirring vigorously. The separated white solid was filtered, triturated, washed with water, dried over KOH and purified by washing with n-hexane, adding 200 ml of solvent under strong stirring. The mixture was filtered, the solid was discarded and the solvent was evaporated to dryness to obtain 2,4-dichloro-3-methyl-benzenesulfonyl chloride as a crystalline white solid. Yield: 85%.
Workup
- addition