2,3,4-Trifluorobenzoic acid → 2-(4-Butyl-2-fluoroanilino)-3,4-difluorobenzoic acid

Participants

Reaction Steps

2,3,4-Trifluorobenzoic acid and 4-butyl-2-fluoroaniline were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B, affording crude 2-(4-butyl-2-fluoroanilino)-3,4-difluorobenzoic acid after workup. The crude material was further purified by flash chromatography on silica (10% EtOAc/Hexane as eluant) to give the desired compound (40%). 1H NMR [400 MHz, CH3OD] δ 7.86 (ddd, J=8.4, 5.8, 2.1 Hz, 1 H), 6.96-6.86 (m, 3 H), 6.78 (ddd, J=9.4, 9.4, 7.1 Hz, 1 H), 2.58 (t, J=7.7 Hz, 2 H), 1.63-1.55 (m, 2 H), 1.36 (sextet, J=7.4, 2 H), 0.94 (t, J=7.5, 3 H). LCMS (ACPI+) 329 (100%).

Provenance & Evidence