Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)- → 4-Propyl-3-(trifluoromethyl)aniline

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To a solution of 1-allyl-4-nitro-2-(trifluoromethyl)benzene (750 mg, 3.24 mmol) in 18 mL of THF and 3.6 mL of H2O was added 10% Pd/C (250 mg, 3.24 mmol). The reaction was stirred at room temperature under an H2 balloon for 24 hr. After filtering to remove Pd/C, the reaction solution was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, 100% Heptane-10% Ethyl Acetate/90% Heptane, to give 4-propyl-3-(trifluoromethyl)aniline (440 mg). LCMS retention time=1.53 minutes (LC method 3); MS (m+1)=203.8. 1H NMR (400 MHz, DMSO-d6) δ 0.93 (t, J=7.4 Hz, 3H), 1.54 (sxt, J=7.6 Hz, 2H), 2.51-2.56 (m, 2H), 5.66 (s, 2H), 6.44 (dd, J=8.5, 1.9 Hz, 1H), 6.52 (d, J=2.1 Hz, 1H), 7.24 (d, J=8.6 Hz, 1H).

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