Potassium Carbonate → 4-{4-[3-Benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxymethyl}benzoic acid

Participants

Reaction Steps

A solution of [4-(4-hydroxyphenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl) methanone (0.5 g, 1.3 mmol), methyl 4-bromomethylbenzoate(0.30 g, 1.3 mmol) and K2CO3 (0.42 g, 3 mmol) in acetone (20 ml) was heated to reflux. After 1 hr, the reaction was cooled, filtered and concentrated. The resulting oil was dissolved in THF/MeOH (20 ml) and treated with 2N NaOH (2 ml) and heated to reflux. After 1 hr, the reaction was cooled, poured into 2N HCl and extracted with EtOAc. The organic layer was dried, concentrated to give a solid which was triturated with 10% EtOAc/hexane, filtered to give the desired compound (0.32 g, Yield=47%); MS (ESI) m/z 528 ([M+H]+); 1H NMR (DMSO) δ 12.98 (bs, 1H), 9.11 (s, 1H), 8.33 (d, 1H, J=6.8 Hz), 7.96-7.91 (m, 3H), 7.82-7.77 (m, 1H), 7.64-7.53 (m, 5H), 7.39-7.35 (m, 2H), 7.27 (d, 2H, J=7.8 Hz), 6.99 (d, 2H, J=7.8 Hz), 5.17 (s, 2H).

Provenance & Evidence