[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 (12.07 g, 0.215 mol) was added to a solution of 2,6-dichloro-3-nitrobenzenesulfonic acid dihydrate (44.35 g, 0.144 mol) in MeOH (850 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 vacu overnight. To this was added PCl5 (30.00 g, 0.144 mol) followed by POCl3 (475 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 (40.42 g, 97%). 1H NMR (DMSO-d6); 7.88 (d, 1H), 7.75 (d, 1H).
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