1,2-Bis(chloromethyl)benzene → 7-Chloro-2-[5-(2-chloromethylbenzyloxy)benzofuran-2-yl]quinoline

Participants

Reaction Steps

To a cooled suspension of 7-chloro-2-(5-hydroxybenzofuran-2-yl)quinoline (0.71 g) in tetrahydrofuran (12 ml), sodium hydride (60% in mineral oil, 0.125 g) was added below 10° c. After being stirred for 15 minutes, α,α'-dichloro-o-xylene (1.68 g) was added to the mixture. After subsequently being stirred at ambient temperature for 1.5 hours, the mixture was refluxed for 25 hours. After the solvent was removed under reduced pressure, the residue was subjected to column chromatography on silica gel (25 g) and eluted with a mixture of chloroform and n-hexane (1:1). The fractions containing object compound were combined and concentrated under reduced pressure give 7-chloro-2-[5-(2-chloromethylbenzyloxy)benzofuran-2-yl]quinoline (0.56 g).

Provenance & Evidence