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-75540f00f0b54420b360c724d7d1ff37

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921514B2