[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:9]2[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH:10]=2)[C:3]1=[O:16].BrBr.O>ClCCl>[OH:15][C:11]1[CH:10]=[C:9]([CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][N:2]([CH3:1])[C:3]2=[O:16])[CH:14]=[CH:13][CH:12]=1A solution of hexahydro-1-methyl-3-(3-oxocyclohexen-1-yl)-2H-azepin-2-one (150 g) in dichloromethane (750 ml) was warmed to 25° C. Bromine (97.5 g) was added over 40 minutes at 25°-32° C. (occasional water cooling being applied) and the mixture stirred for 2 hours at about 25° C. Water (200 ml) was added and the dichloromethane layer washed with water (100 ml). The aqueous phases were combined and extracted into dichloromethane (2×100 ml). The dichloromethane extracts were combined and the solvent distilled off and replaced with ethyl acetate to keep temperature of 72° C. (750 ml ethyl acetate added; 90 ml distillate collected). The mixture was cooled to room temperature and filtered. The product was washed with 100 ml ethyl acetate and dried to give the title compound (134.3 g) as a crystalline fawn powder, m.p. 184°-189° C. Identical to product of Example 4.
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