Azobisisobutyronitrile → HCID 66591479, compound

Participants

Reaction Steps

The above solution of 2-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole (4.8 g, 22 mmol), NBS (11.9 g, 66.9 mmol), and AIBN (0.18 g, 1.12 mmol) in CCl4 (200 mL) was refluxed for 16 h. The resulting solution was filtered and the filtrate was washed with aqueous 10% Na2S2O3 (3×150 mL), brine (100 mL), dried (Na2SO4), and concentrated. The resulting residue was recrystallized from hexanes (350 mL) to provide 3.2 g of 5-bromo-2-(4-(trifluoromethyl)phenyl)oxazole as a crystalline solid. The filtrate and mother liquor was concentrated and purified by flash chromatography over (SiO2, 100:0-90:10 hexanes-EtOAc). to furnish an additional 1.8 g: LCMS (m/z): 294.0 (MH+), tR=1.14 min.

Provenance & Evidence