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 transferred to a separatory funnel 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. 1H NMR (500 MHz, CDCl3): δ 3.54 (br s, 2H), 3.81 (s, 3H), 6.60 (dd, J=8.5, 2.5, 1H), 6.74 (d, J=8.5, 1H), 6.93 (d, J=2.5, 1H).

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 filtrate was transferred to a separatory funnel
6. customthe layers were separated
7. washThe organic layer was washed with 50 mL of sat'd NaHCO3, 50 mL
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo

ORD record

ord-738a453431b74e859d3cb6012401c858

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05877191