Ethanol → 2-(Benzyloxy)-4-fluoroaniline

Temperature

100 °C

To an ethanol (25 mL)-water (25 mL) mixture containing 2-(benzyloxy)-4-fluoro-1-nitrobenzene obtained were added iron (2.79 g, 50.0 mmol) and ammonium chloride (535 mg, 10.0 mmol) at room temperature, and the mixture was stirred at 100° C. for 1 hr. After cooling to room temperature, the reaction mixture was filtered through Celite (registered trademark) and the filtrate was concentrated under reduced pressure. Saturated aqueous sodium hydrogen carbonate solution was added to the resulting residue, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as a brownish red oil (1.26 g).

1. customobtained
2. temperatureAfter cooling to room temperature
3. filtrationthe reaction mixture was filtered through Celite (registered trademark)
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionSaturated aqueous sodium hydrogen carbonate solution was added to the resulting residue
6. extractionthe mixture was extracted three times with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationthe desiccant was filtered off
10. concentrationfollowed by concentration under reduced pressure
11. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

ORD record

ord-d925c7f160fe43ee83497d4eb1e808fe

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09035059B2