Water → 5-Amino-2-fluorophenylacetic acid

Temperature

80 °C

To a suspension of 2-(2-fluoro-5-nitrophenyl)acetic acid (15.0 g, 75.3 mmol) in ethanol (800 mL), THF (400 mL), and water (200 mL) was added ammonium chloride (4.46 g, 83.4 mmol) and ferrous powder (25.04 g, 405.4 mmol). The resulting mixture was heated at 80° C. for 1 hr and the progress of the reaction was monitored by TLC. Upon complete consumption of starting material, the reaction mixture was filtered off while it was hot. The filtrate was evaporated under vacuum and the crude residue was diluted with ethyl acetate (200 mL) and washed with water (3×100 mL). The combined organic layer was washed with brine, dried over Na2SO4 and evaporated under vacuum to afford 2-(5-amino-2-fluorophenyl)acetic acid as a grey solid which was used for the next step without further purification (6.13 g, 48%).

1. customUpon complete consumption of starting material
2. filtrationthe reaction mixture was filtered off while it
3. customThe filtrate was evaporated under vacuum
4. additionthe crude residue was diluted with ethyl acetate (200 mL)
5. washwashed with water (3×100 mL)
6. washThe combined organic layer was washed with brine
7. dry with materialdried over Na2SO4
8. customevaporated under vacuum

ORD record

ord-99c594a7c55f40a2a832598931c42781

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450363B2