[OH-].[K+].O.O.[Cl:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[S:16]([OH:19])(=O)=[O:17].P(Cl)(Cl)(Cl)(Cl)[Cl:21].O=P(Cl)(Cl)Cl>CO>[Cl:5][C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[C:8]([Cl:15])[C:7]=1[S:16]([Cl:21])(=[O:19])=[O:17]
Potassium hydroxide (11.54 g, 0.206 mol) was added to a solution of 2,6-dichloro-3-nitrobenzenesulfonic acid dihydrate (37.38 g, 0.137 mol) in MeOH (500 mL) and the reaction was allowed to stir at room temperature for 14 hr. The reaction mixture was concentrated and the resulting solid was dried in vacuo overnight. To this was added PCl5 (29.60 g, 0.142 mol) followed by POCl3 (400 mL) and the mixture was refluxed overnight. The reaction was then cooled to room temperature and concentrated. The resulting mixture was taken up in EtOAc and chilled in an ice bath. Ice chunks were slowly added to the reaction mixture to quench any leftover PCl5. When bubbling ceased, water was added and the reaction mix was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated to yield 2,6-Dichloro-3-nitrobenzenesulfonyl chloride (31.4 g, 79%).
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