Allyltributylstannane → 5-Allyl-2,1,3-benzoxadiazole

Participants

Reaction Steps

5-Bromo-2,1,3-benzoxadiazole (10 g, 50.3 mmol) was dissolved in toluene (300 mL) and treated with lithium chloride (6.39 g, 151 mmol), Pd(Ph3P)4 (2.90 g, 2.51 mmol), and allyltributylstannane (18.66 ml, 60.3 mmol). Degassed and refluxed the mixture under N2 for 3 hrs. The reaction mixture turned black. Poured the reaction mixture into water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried, and evaporated to dryness. The residue was chromatographed through 120 g ISCO Redi-Sep column and eluted with 0-10% ethyl acetate/hexane to yield 5-(prop-2-en-1-yl)-2,1,3-benzoxadiazole.

Provenance & Evidence