Phenol → 2-Nitro-5-phenoxypyridine

Participants

Reaction Steps

Phenol (306 mg) was dissolved in dry DMF (5 mL) and subsequently, sodium hydride (60% in mineral oil, 130 mg) was added which resulted in strong hydrogen gas evolution. The mixture was then allowed to stir at RT for 30 minutes. Subsequently, 5-bromo-2-nitro-pyridine (600 mg) was added und the resulting mixture was stirred at 60° C. for 12 hours. The reaction mixture was poured into ice water and the aqueous phase was saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give 2-nitro-5-phenoxy-pyridine as a light yellow foam (267 mg). MS (EI): 216.1 (M+).

Provenance & Evidence