Hydrochloric Acid → 3-Bromo-4-methoxyaniline

To a mixture of 2-bromo-4-nitroanisole (5.0 g, 21.5 mmol, Lancaster), ethanol (25 mL) and water (25 mL), was added powdered iron (4.8 g, 86 mmol) and 12 N HCl (0.5 mL). The solution was heated at reflux for 20 minutes. 1N NaOH (10 mL) was added and the reaction mixture was filtered through a pad of celite while still hot, and then rinsed with ethanol (2×50 mL). The ethanol was removed under reduced pressure and the residue extracted with dichloromethane (2×100 mL). The organic extracts were dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on silica gel (75 g) eluting with dichloromethane, to give 4-amino-2-bromoanisole as a light tan solid.

1. temperatureThe solution was heated
2. temperatureat reflux for 20 minutes
3. filtrationthe reaction mixture was filtered through a pad of celite while still hot, and
4. washthen rinsed with ethanol (2×50 mL)
5. customThe ethanol was removed under reduced pressure
6. extractionthe residue extracted with dichloromethane (2×100 mL)
7. dry with materialThe organic extracts were dried (Na2SO4)
8. concentrationconcentrated
9. customThe crude product was purified by flash chromatography on silica gel (75 g)
10. washeluting with dichloromethane

ORD record

ord-08312c05fd27472c88044adf5d417f37

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582765B2