6-Fluoro-2-aminophenol synthesis

Yield:53981-25-2 87%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol; for 1 h;

Steps:

2-amino-6-fluorophenol (KR-400F)

To a of solution of 2-fluoro-6-nitrophenol (6.37 mmol, 1.00 g) in methanol (100 mL), 10% palladium on activated carbon (10 wt% of 2-fluoro-6-nitrophenol,0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a red solid. Silica gel column chromatography (1:1 hexanes/chloroform) provided a crystalline white solid in an 87% yield.

References:

Rynearson, Kevin D.;Charrette, Brian;Gabriel, Christopher;Moreno, Jesus;Boerneke, Mark A.;Dibrov, Sergey M.;Hermann, Thomas [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 15,p. 3521 - 3525] Location in patent:supporting information