Phosphorus oxychloride → 6-Bromo-4-chloro-3-phenyl-2-(trifluoromethyl)quinoline

Participants

Reaction Steps

A solution of 6-bromo-3-phenyl-2-(trifluoromethyl)quinolin-4-ol (8.29 g, 22.5 mmol, Intermediate 19: step a) in phosphoryl trichloride (25 mL, 269 mmol) was heated at 110° C. for 2 hours, and concentrated in vacuo. Dichloromethane and ice-water were added, and the mixture was basified at 4° C. with concentrated NH4OH until pH˜10. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried (Na2SO4), concentrated, and purified by flash column chromatography (120 g silica gel column, 2-9% EtOAc in heptanes) to afford the title compound as a light yellow solid.

Provenance & Evidence