Trifluoroacetic acid → Ethyl 3-fluoro-4-nitro-5-benzyloxyphenylacetate

Participants

Reaction Steps

In methylene chloride (30 ml) was dissolved tert-butyl ethyl 5-benzyloxy-3-fluoro-4-nitrophenylmalonate (2.89 g, 6.67 mmol) . To the resulting solution was added trifluoroacetic acid (30 ml). The resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was distilled under reduced pressure to remove the solvent. The residue was neutralized with an aqueous saturated solution of sodium bicarbonate, 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, whereby from ethyl acetate/hexane (1/5) eluate fractions, ethyl 5-benzyloxy-3-fluoro-4-nitrophenylacetate (1.57 g, 70%) was obtained as a yellow oil.

Provenance & Evidence