Trifluoroacetic anhydride → 2,2,2-Trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide

Participants

Reaction Steps

To the solution of 4-nitrophenethylamine hydrochloride (50 g, 0.247 mole), DIEA (128 mL, 0.74 mole, 3 eq.) and CH2Cl2 (500 mL) in a 1 L round bottom flask equipped with a magnetic stir bar was added (CF3CO)2O (52.5 mL, 0.37 mole, 1.5 eq) drop wise at 5-10° C. (with ice/water bath). After stirring for another 1 h after the addition at RT, the mixture was quenched with water (200 mL) and transferred into a separation funnel. The organic layer was separated, washed with water and sat. NH4Cl, then dried over Na2SO4, filtered, concentrated to give a brown oil. The crude was triturated with water (300 mL), filtered and dried on vacuum overnight to give desired 2,2,2-trifluoro-N-[2-(4-nitro-phenyl)-ethyl]-acetamide as a yellow solid. This was used for next step without further purification. Analytical sample was obtained through recrystallization from CH3OH/H2O as a yellow solid.

Provenance & Evidence