2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Benzofuran-7-carbaldehyde

Participants

Reaction Steps

0.950 g (6.4 mmol) of 7-formyl-2,3-dihydrobenzofuran, 1.82 g (8 mmol) of 2,3-dichloro-5,6-dicyanocyclohexa-2,5-diene-1,4-dione (DDQ) and 30 ml of dioxane are introduced into a 100 ml three-necked flask equipped with a reflux condenser. Heating is carried out at reflux for 24 hours. 100 ml of a molar sodium hydroxide solution are added and extraction is carried out with ethyl ether (3×80 ml). The organic phases are combined, dried and concentrated under vacuum. The residue is purified by silica flash chromatography (elution: 5% ethyl acetate in petroleum ether). 215 mg of 7-formylbenzofuran are obtained in the form of a yellow oil (Yield: 23%).

Provenance & Evidence