Ammonium Chloride → 4-Bromo-5-fluoro-1,2-benzenediamine

Temperature

95 °C

To a solution of 4-bromo-5-fluoro-2-nitroaniline (1.0 g, 4.3 mmol) in THF (9.0 mL), EtOH (9.0 mL) and H2O (3 mL) was added iron powder (1.2 g, 21.3 mmol) and ammonium chloride (0.34 g, 6.4 mmol), and the mixture was heated at 95° C. for 4 hours. The cooled mixture was diluted with EtOH, filtered through diatomaceous earth until no further color came through the filter, and concentrated. The residue was dissolved in EtOAc, washed with H2O, brine, dried (Na2SO4), filtered and concentrated. Hexane was added and the resulting solid collected by filtration to give the title compound (710 mg, 3.5 mmol, 81%).

1. filtrationfiltered through diatomaceous earth until no further color
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with H2O, brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. additionHexane was added
9. filtrationthe resulting solid collected by filtration

ORD record

ord-e7f861ad213e434b9142597c4676a43c

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394279B2