O.O.O.O.O.O.[S:7]([O-:11])([O-])(=[O:9])=S.[Na+].[Na+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23]Cl.[Cl:26]Cl>C(O)(=O)C>[C:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][S:7]([Cl:26])(=[O:11])=[O:9])([O:15][CH3:14])=[O:25]
A mixture of water (50 ml) and 29.5 g of sodium thiosulfate pentahydrate was added to o-(chloromethyl)benzoic acid methyl ester 20 g, and stirred for 5 hours at 50˜55° C. 300 ml of acetic acid was added and then excess of chlorine gas for 3 hours was infused, while maintaining the internal temperature of reactor at 5˜10° C. The reaction mixture was further stirred for 1 hour at the same temperature. Excess of chlorine gas was removed via infusion of nitrogen gas and with the addition of ice water (300 ml), stirred for 30 minutes. A solid, so formed, was filtered with a cold water and dried to afford 22.4 g of desired compound (yield 83%) as a white solid.
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