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ChemicalBook CAS DataBase List 6-Fluoro-2-aminophenol
53981-25-2

6-Fluoro-2-aminophenol synthesis

1synthesis methods
2-Fluoro-6-nitrophenol

1526-17-6

6-Fluoro-2-aminophenol

53981-25-2

The general procedure for the synthesis of 6-fluoro-2-aminophenol from 2-fluoro-6-nitrophenol was as follows: 2-fluoro-6-nitrophenol (6.37 mmol, 1.00 g) was dissolved in methanol (100 mL), and 10% activated charcoal-loaded palladium catalyst (10% by weight of 2-fluoro-6-nitrophenol, 0.10 g) was added. The reaction system was displaced first with argon and then with hydrogen, each displacement lasting 15 min, during which magnetic stirring was maintained. Subsequently, the reaction was carried out at atmospheric pressure (using a hydrogen balloon) and under hydrogen atmosphere for 1 hour. Upon completion of the reaction, the gas in the reaction vessel was again replaced with argon for 15 minutes. The reaction mixture was filtered through a diatomaceous earth pad and washed with methanol (50 mL). The filtrate was concentrated under vacuum to give a red solid product. Purification by silica gel column chromatography (eluent ratio 1:1 hexane/chloroform) gave a white crystalline solid in 87% yield.

-

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

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