C=C.[Cl:3][C:4]1[C:13]([CH:14]=[N:15][OH:16])=[C:12]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7].[C:21]([O-])(=O)[CH3:22].[Na+].Cl[O-].[Na+]>ClCCl>[Cl:3][C:4]1[C:13]([C:14]2[CH2:22][CH2:21][O:16][N:15]=2)=[C:12]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]At 15-20° C., ethylene is introduced into a solution of 158.0 g (0.54 mol) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 1 l of dichloromethane for 30 minutes. After the addition of 1.6 g of sodium acetate, 454 ml of sodium hypochlorite solution were added dropwise at 10° C., while simultaneously introducing ethylene. Subsequently, ethylene was introduced at 10° C. for a further 15 minutes. The mixture was stirred for 12 hours, the phases were separated and the organic phase was washed with water, dried and concentrated. 156.5 g (90% of theory) of methyl 2-chloro-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate were obtained.
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