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1236410-18-6

4-(3,3,3-trifluoropropyl)aniline synthesis

4synthesis methods
Benzene, 1-nitro-4-[(1E)-3,3,3-trifluoro-1-propen-1-yl]-

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4-(3,3,3-trifluoropropyl)aniline

1236410-18-6
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Yield:1236410-18-6 47%

Reaction Conditions:

with hydrogen;20 % Pd(OH)2/C in ethanol;ethyl acetate at 20; under 2585.81 Torr; for 20 h;Inert atmosphere;

Steps:



(E)-1-nitro-4-(3,3,3-trifluoroprop-1-enyl)benzene (510 mg, 2.35 mmol) was dissolved in ethanol (15 mL) and ethyl acetate (15 mL). 20% Palladium hydroxide on carbon (250 mg) was carefully added to reaction vessel under a steady stream of nitrogen. The reaction was stirred in a parr shaker at room temperature under hydrogen (50 PSI) for 20 hours. The reaction mixture was filtered through a pad of celite and filtrate concentrated. Crude oil was purified on silica gel, eluding with a gradient from 5% to 40% ethyl acetate in heptane to give 4-(3,3,3-trifluoropropyl)benzenamine (210 mg, 47%). GCMS was 189 at 1.35 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.22-2.42 (m, 2H) 2.68-2.80 (m, 2H) 3.57 (br. s., 2H) 6.59-6.66 (m, 2H) 6.91-7.01 (m, 2H)

References:

US2010/197591,2010,A1 Location in patent:Page/Page column 44