2-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene → HCID 86666596, compound

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Reaction Steps

2-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene (2) (1.00 g, 3.30 mmol) was dissolved in MeOH (150 mL) and passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The solvent was removed in vacuo and the residue was dissolved in EtOH (20 mL) and then treated with 10% Pd/C (182 mg, 171 μmol). Hydrogen gas was bubbled through the mixture, with stirring at RT for 2 h. The mixture was then filtered through Celite and concentrated in vacuo. The residue was purified by silica gel chromatography (15% EtOAc in isohexane) to afford 4-ethoxy-3,5-bis(trifluoromethyl)aniline (3) (460 mg, 56%) as a white solid: m/z 273 [M+H]+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.09 (2H, s), 5.76 (2H, s), 3.87 (2H, q), 1.29 (3H, t).

Provenance & Evidence