Indole → 3,4-Dichloro-5-(1H-indol-3-yl)furan-2(5H)-one

Participants

Reaction Steps

A stirred mixture of 20.3 g (0.12 mole) of mucochloric acid, 14.1 g (0.12 mole) of indole and 125 ml of benzene was heated for approximately twenty hours at reflux temperature. The reaction mixture was cooled to ambient temperature and a dark brown solid which had separated was collected by filtration. This solid was purified by two successive recrystallizations from benzene at approximately 60° C., with the aid of decolorizing charcoal. After the second recrystallization, the purified product was dried at 60° C. in vacuo to obtain 5.3 g of the known 5-(3-indolyl)-3,4-dichloro-2(5H)-furanone (Formula VI: R=R1 =Y=H), a pale green-colored solid, which first melted at 174° C., then turned black and finally decomposed at 182° C.

Provenance & Evidence