Ammonium Chloride → 4-Amino-2-chloro-5-fluorophenol

Zinc dust (10 g, 160 mmol) was added portion wise to a solution of 2-chloro-5-fluoro-4-nitro-phenol (3.0 g, 16 mmol) and NH4Cl (8.4 g, 160 mmol) in THF (150 mL) and MeOH (150 mL) and the mixture was stirred at RT for 0.5 h. The reaction mixture was filtered, and the filter cake was washed with EtOAc (3×50 mL). The combined filtrate was washed with brine (3×100 mL), dried over Na2SO4 and concentrated to provide 4-amino-2-chloro-5-fluorophenol (2.5 g, 100% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.39 (s, 1 H), 6.76 (d, J=9.2 Hz, 1 H), 6.65 (d, J=12.4 Hz, 1 H), 4.70 (s, 2 H).

1. filtrationThe reaction mixture was filtered
2. washthe filter cake was washed with EtOAc (3×50 mL)
3. washThe combined filtrate was washed with brine (3×100 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated

ORD record

ord-61aa73d63b7a46fc8c9a7e20098235dd

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09387202B2