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

To a solution of potassium 5-chloro-2-fluoro-4-nitrophenolate (1.0 g, 4.35 mmol) in 95% EtOH (22 mL) and H2O (8 mL) was added Fe (0.97 g, 17.4 mmol) and NH4Cl (1.86 g, 34.8 mmol). The mixture was stirred at rt for 10 hours, then diluted with methanol (100 mL) and ethyl acetate (100 mL). Filtered and the filtrate was concentrated in vacuo. The residue was dissolved in water (50 mL) and ethyl acetate (50 mL). The organic phase was separated and the water phase was extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo to give the title compound as a pale solid (0.6 g, 85.3%).

1. filtrationFiltered
2. concentrationthe filtrate was concentrated in vacuo
3. dissolutionThe residue was dissolved in water (50 mL)
4. customThe organic phase was separated
5. extractionthe water phase was extracted with ethyl acetate (50 mL×2)
6. washThe combined organic layers were washed with brine (50 mL×3)
7. dry with materialdried over anhydrous Na2SO4
8. concentrationconcentrated in vacuo

ORD record

ord-246aa66ff61249419f7ea016680380c6

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969388B1