[Br:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[C:6]3([CH3:15])[CH2:13][CH2:12][C:9]([CH3:14])([C:10]=2[CH:11]=1)[CH2:8][CH2:7]3.[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[C:6]3([CH3:15])[CH2:13][CH2:12][C:9]([CH3:14])([CH2:8][CH2:7]3)[C:10]=2[CH:11]=1To a solution of 5-bromo-1,8-dimethyl-tricyclo[6.2.2.02,7]dodeca-2(7),3,5-trien-4-ol (Compound 3, 0.825 g, 2.94 mmol) in 10 mL of anhydrous acetone was added potassium carbonate (0.128 g, 8.82 mmol) and iodomethane (0.1 mL, 8.82 mmol). The reaction mixture was stirred at 25° C. for 12 hours and filtered. The filtrate was concentrated, and then it was diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:hexane (5:95) to yield the title compound as a white solid.
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