2-Bromo-4-nitroanisole → 3-Bromo-4-methoxyaniline

Temperature

80 °C

A mixture of 670 mg (2.9 mmol) of 2-bromo-4-nitroanisole and 1.20 g (21.1. mmol) of iron powder in 10 mL of 1:1 v/v HOAc/H2O was heated at 80° C. for 1.5 h. The mixture was cooled and filtered onto a pad of Celite. The flask and filtered solids were rinsed with 100 mL of EtOAc and 100 mL of H2O. The filtrate was transfered to a separatory fumel and the layers were separated. The organic layer was washed with 50 mL of sat'd NaHCO3, 50 mL sat'd NaCl, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 25 g of silica gel using 3:2 v/v hexanes/ether as the eluant afforded 504 mg (86%) of the title compound as an oil.

1. temperatureThe mixture was cooled
2. filtrationfiltered onto a pad of Celite
3. filtrationThe flask and filtered solids
4. washwere rinsed with 100 mL of EtOAc and 100 mL of H2O
5. customthe layers were separated
6. washThe organic layer was washed with 50 mL of sat'd NaHCO3, 50 mL
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-a0c30345ef4c419390b9482b190cf44b

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929094