Hydrochloric Acid → 3-(Benzyloxy)-6-chloro-2-iodopyridine

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Reaction Steps

To an aqueous solution (100 mL) of 2-chloro-5-hydroxypyridine (10.0 g) were added sodium carbonate (16.3 g) and iodine (10.8 g), and the mixture was stirred at room temperature for 5 days. The reaction mixture was acidified to pH=5 with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a yellow solid. The obtained solid was recrystallized from methanol to give a brown solid. To a solution (200 mL) of the obtained solid in acetone were added benzyl bromide (8.02 mL) and potassium carbonate (15.5 g), and the mixture was stirred overnight with heating under reflux. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-30% ethyl acetate/hexane) to give the title object compound (18.4 g, 69%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 5.17 (s, 2H), 6.97 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.30-7.47 (m, 5H).

Provenance & Evidence