Iodine → HCID 11118595, compound

Participants

Reaction Steps

To a solution of 4.3 g (25 mmol) of p-bromotoluene in 75 ml of ether cooled to 5° was dropwise added 15 ml of a 1.6M solution of butyl lithium in hexane, while maintaining the temperature below 5°. This mixture was stirred at 5° for 10 min. and at 30° for 10 min., and then cooled to -20°. A solution of 3.4 g (20 mmol) of 4-chloroquinoline in 15 ml of ether was added while maintaining the temperature at -20°. It was allowed to warm to room temperature during 15 min. To the reaction mixture was then added 10 ml of water and 5 g of iodine, and 60 ml of 3N sodium hydroxide. After 20 min. of stirring the organic layer was separated. The aqueous phase was extracted with an equal volume of ether in three portions. The organic phases were combined, washed with water, dried over sodium sulfate, and concentrated in vacuo to leave an oil. This oil was dissolved in methylene chloride and the solution filtered through a plug of alumina. The filtrate was concentrated in vacuo to give 2.6 g of product mp 75°-77°, as off-white needles.

Provenance & Evidence