Sodium hydride → 4-(4-Bromo-3-fluorophenoxy)-2-methylpyridine 1-oxide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromo-3-fluorophenol (6 g, 31.41 mmol) in DMF (20 ml) was added NaH (0.81 g, 56 mmol, 60% in mineral oil) at room temperature. The resulting reaction mixture was stirred for 10 min., then, 4-nitro-2-picoline N-oxide (5.6 g, 36.12 mmol) was added. The resulting solution was subjected to microwave heating at 180° C. for 1 h. The mixture was cooled to room temperature and diluted with EtOAc and H2O. Layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue thus obtained was purified by column chromatography (silica gel; DCM/MeOH(NH3) up to 2% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound D14 (3.61 g, 39%) as dark orange solid.

Provenance & Evidence