2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 13370663, compound

Participants

Reaction Steps

To a solution of 13.91 g. of 1-[4,5-bis(4-methoxyphenyl)-1,5-cyclohexadien-1-yl]-4-fluorobenzene in 500 ml. of toluene were added 9.08 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The solution was allowed to reflux under a nitrogen atmosphere for 20 hours employing a Dean-Stark trap. After cooling, the reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by chromatography. The appropriate fractions were combined, evaporated, and recrystallized from diethyl ether/Skelly B to provide 6.08 g. of the desired product as a yellow solid, m.p. about 107°-110° C.

Provenance & Evidence