2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 2-(benzofuran-3-yl)acetate

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A toluene solution under N2 atmosphere containing ethyl 2,3-dihydrobenzo[b]furan-3-acetate (9.80 g, 47.6 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (12.97 g, 57.1 mmol) was heated at reflux for ~8 h. The reaction was filtered and the filtrate concentrated in vacuo. Silica gel chromatography (97:3 Hexane:EtOAc) of the residue afforded the title compound (7.24 g, 75%) as an orange oil.

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