[N+]([O-])(O)=O.[Cl:5][C:6]1[C:7]([F:16])=[C:8]([CH:12]=[CH:13][C:14]=1[F:15])[C:9]([OH:11])=[O:10].[Br:17]Br>C(O)(=O)C.O.[N+]([O-])([O-])=O.[Ag+]>[Br:17][C:13]1[C:14]([F:15])=[C:6]([Cl:5])[C:7]([F:16])=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]In a mixture of 50 ml of acetic acid, 10 ml of water and 13 ml of nitric acid is dissolved 2 g (0.014 mole) of 3-chloro-2,4-difluorobenzoic acid and 3.64 ml (0.028 mole) of bromine. A solution of 3.52 g (0.0208 mole) of silver nitrate in 10 ml of water is then added slowly. After 14 hours at 20° C., the precipitate is filtered and rinsed with ether. The organic phase is washed with sodium bisulfite, then water and dried. Removal of the solvent affords the desired product.
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