Cesium carbonate → Methyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(2,2,2-trifluoroethyl)glycinate

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Reaction Steps

A mixture of 4-(2,2,2-trifluoro-ethylamino)-2-trifluoromethyl-benzonitrile (5.00 g, 18.7 mmol), methyl bromoacetate (3.25 mL, 37.5 mmol), and Cs2CO3 (12.2 g, 37.3 mmol) in acetonitrile (50 mL) was held at reflux, under N2, for 2 h and cooled to rt, and solids were removed by filtration. The filtrate was adsorbed onto a minimal amount of silica gel, filtered through a short pad of silica gel (EtOAc/hexanes) and concentrated to dryness. Recrystallization from EtOAc/hexanes afforded 4.72 g of the title compound as fine needles, mp 144-145° C.: 1H NMR (400 MHz, CDCl3) δ 7.69 (d, J=8.9 Hz, 1H), 7.01 (d, J=2.3 Hz, 1H), 6.88 (dd, J=2.6 Hz, 1H), 4.24 (s, 2H), 4.06 (q, J=8.5 Hz, 2H), 3.81 (s, 3H).

Provenance & Evidence