Water → 5-[4-(4-Methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

Participants

Reaction Steps

A mixture of 1.00 g (3.74 mmol) of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester and 0.775 g (4.12 mmol) of 4-(4-methoxymethyl-phenyl)-1H-imidazole in 10 ml of tetrahydrofuran are refluxed for 2 hours. After cooling, the reaction mixture is distributed between ethyl acetate and water, the organic phase separated and washed with brine, dried over Na2SO4 and concentrated to dryness. The residue is purified by flash chromatography on silica (40-63 μm particle size) with ethyl acetate/hexane 2:3, yielding 1.55 g of 5-[4-(4-methoxymethyl-phenyl)-imidazol-1-yl]-2-nitro-4-trifluoromethyl-benzoic acid methyl ester acid as a yellow powder, m.p.=135-137° C. 1H-NMR (DMSO-d6, 400 MHz): 3.30 s, 3H; 3.95 s, 3H; 4.42 s, 3H; 7.35 d, J 10.4 Hz, 2H; 7.82 d, J=10.4 Hz, 2H; 8.02 s, 1H; 8.05 s, 1H; 8.30 s, 1H; 8.72 s, 1H.

Provenance & Evidence