Nitrogen → 5-(Phenylthio)benzo[d]oxazole

Participants

Reaction Conditions

Reaction Steps

A 150 mL pressure bottle was charged with 5-bromobenzo[d]oxazole (2.43 g, 12.3 mmol), N,N-diisopropylethylamine (4.28 mL, 24.5 mmol), and 24 mL dioxane. N2 was bubbled through the solution for 3 min, at which point tris(dibenzylidineacetone)palladium(0) (0.281 g, 0.307 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.355 g, 0.614 mmol), and benzenethiol (1.26 mL, 12.3 mmol) were added. The dark brown solution was sealed and heated to 100° C. overnight. The mixture was diluted with EtOAc and NaOH, and the organic layer was extracted 2×1N NaOH. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give an orange oil, which was purified by ISCO, 0-100% 10% EtOAc/hexanes in hexanes to give 5-(phenylthio)benzo[d]oxazole as an orange oil. MS (ESI) m/z: Calculated: 227.0; Observed: 228.0 (M++1).

Provenance & Evidence