[Cl-].[CH3:2][O:3][C:4]1([O:14][CH3:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=[N:12][OH:13].Cl.[Br:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)C>[Br:17][CH:11]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5](=[N:12][OH:13])[C:4]1([O:3][CH3:2])[O:14][CH3:15]Following the general procedure of Example 1, but using diethyl ether as a solvent in place of methylane chloride, to a solution of 5.025 parts of 2,2-dimethoxycyclooctanone oxime in 28 parts of diethyl ether was added 1.7 parts anhydrous hydrogen chloride at about 32° C. The mixture was stirred and to this was added about 4 parts bromine dissolved in 7 parts diethyl ether over a 5 minute period. After the addition the mixture was allowed to stir for about 0.5 hour. The mixture was then treated with aqueous sodium carbonate to remove dissolved acids in the ether layer and then worked with water. The ether phase was then dried and then distilled under vacuum to yield 50 percent of theory of 3-bromo-2,2-dimethoxycyclooctanone oxime as determined by nuclear magnetic resonance spectroscopy.
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