Ammonium Chloride → 5-Bromo-3-fluorobenzene-1,2-diamine

Temperature

95 °C

To a solution of 4-bromo-2-fluoro-6-nitroaniline (0.5 g, 2.1 mmol) in THF (4.6 mL), EtOH (4.6 mL) and H2O (1.5 mL) was added iron powder (0.6 g, 10.6 mmol) and ammonium chloride (0.17 g, 3.2 mmol). The resulting mixture was stirred at 95° C. for 22 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 and the residue was dissolved in EtOAc, washed with H2O and brine, dried over Na2SO4, filtered and concentrated to give the title compound (0.43 g, 99%) as a brown, waxy solid.

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
5. dissolutionthe residue was dissolved in EtOAc
6. washwashed with H2O and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-6aed12fd618d46588f3cafd18ab24fbb

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394279B2