Ethanol → Benzo(c)(1,2,5)oxadiazole-5-carbaldehyde

Participants

Reaction Steps

AgNO3 (163 g) in 2 L of water was added to a refluxing mixture of dibromomethylbenzofurazan (122 g, 418 mmol) in EtOH (1 L). Heating at reflux temperature was continued for 2 h. The mixture was cooled, the precipitated AgBr was removed by filtration through Celite, and the solvent was concentrated. The resulting solution was extracted with toluene (10×100 mL), dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was chromatograghed (EtOAc/hexane, 1/125), giving the title aldehyde (48.2 g, 78%) as a white solid: 1H NMR δ 7.92 (m, 2H), 8.39 (s, 1 H), 10.10 (s, 1 H).

Provenance & Evidence