Iodine → 2,5-Dichloro-4-iodopyridine

Participants

Reaction Steps

Under an argon atmosphere, 3 g of 2,5-dichloropyridine was added to 40 ml of tetrahydrofuran, and 11.15 ml of lithium diisopropylamide (2M heptane/tetrahydrofuran/ethylbenzene solution) was added at −78° C. After stirring for 2 hours, 5.66 g of iodine was added, and the mixture was further stirred for 3 hours. The reaction solution was poured into an aqueous saturated sodium thiosulfate solution, and the resultant solution was extracted with tert-butyl=methyl=ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 4 g of 2,5-dichloro-4-iodopyridine.

Provenance & Evidence