Ethanol → 2-(Benzyloxy)-3-fluoro-4-{[6-(methylsulfonyl)pyridin-3-yl]oxy}aniline

Participants

Reaction Steps

A mixture of 5-[3-(benzyloxy)-2-fluoro-4-nitrophenoxy]-2-(methylsulfonyl)pyridine (8.4 g), iron (powder, 5.5 g), calcium chloride (0.24 g), ethanol (200 mL) and water (40 mL) was refluxed for 4 h. The mixture was cooled to room temperature and filtered through a celite pad. The filtrate was concentrated in vacuo to remove ethanol. The residue was partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=20:80 to 40:60, volume ratio) to give the title compound (5.5 g, 70%) as a dark green oil. MS 389 (MH+).

Provenance & Evidence