3-Nitroaniline → (3-Fluoro-2-nitro-phenyl)-(3-nitro-phenyl)-amine

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Reaction Steps

To a solution of 3-nitro-phenylamine (1.82 g, 0.013 mol) in DMF (8 ml) at 0° C. is added NaH (60% dispersion in mineral oil, 0.53 g, 0.013 mol). The reaction is stirred at this temperature for 15 min. Subsequently, a solution of 1,3-difluoro-2-nitro-benzene (0.70 g, 4.4 mmol) in DMF (2 ml) is added slowly. After stirring for additional 30 min, it is poured into a saturated aqueous solution of NH4Cl. The precipitate therefore formed is collected by vacuum filtration. The desired compound is obtained after flash column chromatography purification of the precipitate (silica gel, eluted by hexanes-ethyl acetate). 1H NMR (CDCl3) δ 6.77 (dd, 1H, J=10 Hz, J2=10.6 Hz), 7.11 (d, 1H, J=8.8 Hz), 7.35-7.41 (m, 1H), 7.49-7.59 (m, 2H), 7.99 (dt, 1H, J1=8.0 Hz, J2-2.0 Hz), 8.09 (t, 1H, J=2.0 Hz), 8.35 (bs, 1H); LC-MS: 278.0 (MH+).

Provenance & Evidence