Ethanol → Ethyl 2-(3-fluoro-4-nitrophenyl)acetate

Trifluoroacetic acid (25 ml) was added to a solution of di-tert-butyl (3-fluoro-4-nitrophenyl)malonate (5.11 g, 14.4 mmol) in methylene chloride (50 ml). The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to yield a colorless solid substance. To the solid substance were added concentrated sulfuric acid (1 ml) and ethanol (50 ml) and the mixture was heated and refluxed for 2 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Ice water (100 ml) was poured in the residue, followed by extraction with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby ethyl 3-fluoro-4-nitrophenylacetate (3.15 g, 96%) was obtained as a yellow oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customto yield a colorless solid substance
3. temperaturethe mixture was heated
4. temperaturerefluxed for 2 hours
5. temperatureAfter cooling to room temperature
6. concentrationthe reaction mixture was concentrated under reduced pressure
7. additionIce water (100 ml) was poured in the residue
8. extractionfollowed by extraction with ethyl acetate
9. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate
10. dry with materialdried over anhydrous sodium sulfate
11. distillationdistilled under reduced pressure
12. customto remove the solvent

ORD record

ord-7ec54c886a5044ea8652c2fa05073b38

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2