Methanol → 6-Bromo-4-chloro-3-(4-fluorobenzyl)-2-methoxyquinoline

Participants

Reaction Steps

A mixture of 6-bromo-2,4-dichloro-3-(4-fluorobenzyl)quinoline (0.350 g, 0.909 mmol, Intermediate 4: step c) and a 0.5 M sodium methoxide in methanol solution (9.09 mL. 4.55 mmol) was stirred at reflux for 16 hours. The mixture was poured into ice water and extracted with EtOAc (2×). The combined EtOAc extract was dried (Na2SO4), filtered and evaporated in vacuo and purified by column chromatography with silica gel (heptane/CH2Cl2) to provide the title compound as a white solid.

Provenance & Evidence