Iodine → 6-Bromo-2-chloro-3-iodoquinoline

Participants

Reaction Conditions

Reaction Steps

To a solution of THF (50 mL) and DIPA (1.8 mL, 12.37 mmol) at −70° C. was added n-BuLi (7.7 mL, 12.4 mmol). The mixture was allowed to stir at 0° C. for 1 h. Slow addition of 6-bromo-2-chloroquinoline (3.0 g, 12.4 mmol) in THF (50 mL) was achieved at −75° C. and the mixture was stirred at this temperature for 2 h. Iodine (3.1 g, 12.4 mmol) in 10 ml of THF was then slowly added and the reaction mixture was allowed to stir at −75° C. for 2 h before hydrolysis by THF/water (20% v/v). Water and diethyl ether were added at −10° C. and the reaction mixture was extracted with ether. The organic layer was washed with sodium thiosulfate and water, dried over MgSO4 and concentrated in vacuo to give a yellow solid which was slurried with hexane and filtered to give 6-bromo-2-chloro-3-iodoquinoline as a tan solid.

Provenance & Evidence