Iodine → 2,5-Dichloro-4-iodopyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA (11 mL of a 2 M in heptane/THF/ethylbenzene, 22 mmol) in THF (30 mL) at −78° C. was added a solution 2,5-dichloropyridine (3.3 g, 22 mmol) in THF (20 mL) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, and a solution of iodine (5.6 g, 22 mmol) in THF (20 mL) was added. The reaction mixture was stirred for 15 min, quenched with water, and warmed to rt. The reaction mixture was diluted with EtOAc, washed with water (1×), saturated Na2S2O3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The crude reaction mixture was dissolved in dichloromethane (˜50 mL), diluted with hexanes (˜100 mL), and concentrated to a volume of ˜100 mL. The solid was collected by filtration, and washed with hexanes to give 2,5-dichloro-4-iodopyridine.

Provenance & Evidence