Ethanol → 4-Bromo-3-fluorobenzene-1,2-diamine

Temperature

80 °C

To a solution of 4-bromo-3-fluoro-2-nitroaniline (3.0 g, 12.8 mmol) in THF (30 mL) was added EtOH (30 mL) and H2O (10 mL) followed by iron powder (3.6 g, 63.8 mmol) and ammonium chloride (1.0 g, 19.2 mmol). The resulting mixture was stirred at 80° C. for 16 hours. The mixture was cooled to room temperature and filtered through diatomaceous earth. The solid was washed with EtOH until no further color came through the filter. The filtrate was concentrated in vacuo and the crude product was purified by column chromatography on silica gel using a solvent gradient of 0-40% EtOAc in hexane to give the title compound (2.2 g, 84%).

1. temperatureThe mixture was cooled to room temperature
2. filtrationfiltered through diatomaceous earth
3. washThe solid was washed with EtOH until no further color
4. concentrationThe filtrate was concentrated in vacuo
5. customthe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-40% EtOAc in hexane

ORD record

ord-17a1d3fa19b84943894dd5f9ddbcf5b0

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08937150B2