CO.[CH:3]1([O:8][C:9]2[CH:10]=[C:11]([C:17](=[O:19])[CH3:18])[CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br-:20].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.C(=O)([O-])O.[Na+]>O>[Br:20][CH2:18][C:17]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7]2)[CH:10]=1)=[O:19]To 200 ml of methanol solution containing 11.6 g (49.5 mmol) of 1-(3-cyclopentoxy-4-methoxyphenyl)ethanone (see Bioorg. Med. Chem. Lett. 2003, 13, 2355) was added 20.47 g (54.5 mmol) of trimethylphenylammonium tribromide at room temperature, and the mixture was stirred at room temperature for 40 minutes. After completion of the reaction, water was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of sodium hydrogencarbonate and then extracted with chloroform. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. To the obtained concentrate was added 50 ml of a mixed solvent (diisopropyl ether/hexane=1/2 (V/V)), and precipitated solid was collected by filtration. The obtained solid was washed with diisopropyl ether, and dried under reduced pressure to obtain 6.47 g of the title compound as a white solid. (Yield: 41%)
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