Triphenylphosphine → 5-Bromo-3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Participants

Reaction Steps

To a stirred solution of triphenyl phosphine (9.4 g, 0.036 mol) and DIAD (7.2 g. 0.036 mol) in THF (100 mL) at 0° C. was added a solution of (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (4.55 g, 0.021 mol) and 5-bromo-3-hydroxy-2-nitropyridine (3.35 g, 0.023 mol) in THF (200 mL). The resulting bright orange solution was stirred under a nitrogen atmosphere at ambient temperature for 4 hours at which point all starting materials had been consumed. The solvent was removed, and the crude material was dry loaded onto silica gel, and eluted with ethyl acetate-hexanes (20:80) to yield the title compound as a white solid (8.6 g, 85%).

Provenance & Evidence