Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.C([Li])CCC.[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=2)[N:18]=[CH:17][CH:16]=1.II.[OH-].[Na+]>CCOCC.CCCCCC.O1CCCC1.O>[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=2)[N:18]=[C:17]([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=2)[CH:16]=1To a solution of 4.37 g (25 mmol) of 1-bromo-4-fluorobenzene in 35 ml of ether cooled to -10° was added 15 ml of a 1.6M solution of butyl lithium in hexane in portions while maintaining the temperature below 0°. This mixture was stirred below 0° for 15 min. A solution of 3.63 g (20 mmol) of 4-chloro-6-fluoroquinoline in 20 ml of tetrahydrofuran was added while maintaining the temperature below 0°. The dark solution was stirred at room temperature for 20 min. To the reaction mixture was then added 5 ml of water and 5 g of iodine, and 10 ml of 3N sodium hydroxide. After 10 min of stirring the solid was collected to give 2.8 g of product, mp 130°-133°.
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