Iodine → 4,6-Dichloro-2-(4-fluorophenyl)quinoline

Participants

Reaction Steps

To a solution of 5.5 ml (50 mmol) of 1-bromo-4-fluorobenzene in 70 ml of ether cooled to -40° was added 21 ml of a 2.4M solution of butyl lithium in hexane while maintaining the temperature below -15°. This mixture was stirred at -15° for 15 min. A solution of 7.42 g (40 mmol) of 4,6-dichloroquinoline in 40 ml of tetrahydrofuran was added while maintaining the temperature at -20°. It was allowed to warm to 0° during 15 min. To the reaction mixture was then added 10 ml of water and 10.16 g (40 mmol) of iodine, and 15 ml of 3N sodium hydroxide. After 10 min of stirring this mixture was then cooled to 5°, and the solid collected. This solid was dissolved in methylene chloride, and the solution filtered through a plug of alumina. The filtrate was concentrated in vacuo to leave a residue which was crystallized from ethyl acetate to give 5.7g of crude product, mp 150°-156°.

Provenance & Evidence