Iodine → 4-Chloro-2-(4-chlorophenyl)quinoline

Participants

Reaction Steps

To a solution of 15.3 g (80 mmol) of 4-bromochlorobenzene in 100 ml of ether cooled to -25° was added 60 ml of a 1.6M solution of butyl lithium in hexane in three portions while maintaining the temperature below -20°. This mixture was allowed to warm to -5° during 15 min. It was then recooled to -20°, and a solution of 11.45 g (70 mmol) of 4-chloroquinoline in 40 ml of ether was added while maintaining the temperature at -20°. A yellow suspension formed. It was allowed to warm to 0° for 15 min, and was then stirred for a further 20 min at 0°-10°. To the reaction mixture was then added 20 ml of water and 20 g of iodine. After 20 min of stirring 40 ml of 3N sodium hydroxide solution was added and stirring was continued for a further 15 min. This mixture was then cooled to 10°, and the solid collected to give 17.65 g of product, mp 119°-122°.

Provenance & Evidence