Potassium Carbonate → 3-Fluoro-4-nitroaniline

A mixture of N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide (87.0 g, 0.36 mol) in CH2Cl2 (400 mL) and 6N hydrochloric acid (800 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with 1000 mL of ethyl acetate and potassium carbonate (500.0 g) was added portion wise. The aqueous solution was separated and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure; the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to afford 3-fluoro-4-nitroaniline (56.0 g, 99%). 1H NMR (300 MHz, CDCl3) δ 8.07 (t, J=8.7 Hz, 1H), 7.86 (dd, J=2.1, 13.2 Hz 1H), 7.59 (brs, 2H), 7.22 (s, 1H).

1. temperaturewas heated
2. temperatureto reflux for 2 hours
3. additionwas added portion wise
4. customThe aqueous solution was separated
5. washthe organic layer was washed with brine
6. dry with materialdried over anhydrous Na2SO4
7. customThe solvent was removed by evaporation under reduced pressure
8. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1)

ORD-Eintrag

ord-e8b9dc6e851c4217b8b6ea9028b42bb8

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08952049B2