Acetic Acid → Methyl (4-amino-2-fluoro-3-hydroxyphenyl)acetate

Participants

Reaction Steps

Methyl 2-fluoro-3-hydroxy-4-nitrophenylacetate (5.22 g, 14.9 mmol), reduced iron powder (2.66 g, 47.7 mmol), sodium acetate-trihydrate (2.03 g, 14.9 mmol) and acetic acid (5.54 ml) were heated and refluxed at 110° C. for 4 hours in methanol:water (1:4, 300 ml). After cooling to room temperature, the reaction mixture was filtered through Celite under reduced pressure to remove the insoluble matter. The filtrate was then concentrated, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 50 g), whereby from hexane/ethyl acetate (2/1) eluate fractions, the title compound (1.29 g, 44%) was obtained as a brown oil.

Provenance & Evidence