4-Iodophenol → 2-((4-Iodophenoxy)methyl)-6-phenoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of (6-phenoxypyridin-2-yl)methanol (100 mg) in ethyl acetate (4 ml), triethylamine (0.103 ml) and methanesulfonyl chloride (0.062 ml) were added under ice-cooling, the reaction solution was stirred at the same temperature for 1 hour. The reaction solution was diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a brown oil. To a solution of 4-iodophenol in dimethylformamide (1 ml), 24 mg of sodium hydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was cooled to 0° C., a solution of the crude product in dimethylformamide (1 ml) was added, and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was diluted with a saturated saline solution, extracted with diethyl ether, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-20:80)) to afford the title compound as a white solid.

Provenance & Evidence