Trifluoroacetic anhydride → 3-(4-Bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide

Participants

Reaction Steps

To a solution of 5-bromo-N,N-diethyl-2-(2-fluoropyridin-3-yloxy)benzamide (1.4 g, 3.81 mmol) and urea peroxide (1.076 g, 11.44 mmol) in 10 mL of DCM at 0 C was added dropwise trifluoroacetic anhydride (1.601 mL, 11.44 mmol) and the resulting reaction was stirred overnight. LCMS showed only less than 50% of desired conversion. The mixture was evaporated to dryness, quenched with Sat. NaHCO3, extracted with EA, dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified using column chromatography (DCM to DCM/EA=3:1 to DCM/MeOH=100:2 to 100:5 to 100:10) to provide 3-(4-bromo-2-(diethylcarbamoyl)phenoxy)-2-fluoropyridine 1-oxide as an offwhite solid.

Provenance & Evidence