Potassium Carbonate → 2,7-Bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene

Participants

Reaction Conditions

Reaction Steps

A mixture of 17.0 grams of 2,7-diiodo-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene, 4.3 grams of copper bronze, 12.5 grams of potassium carbonate in 30 milliliters of Soltrol 220 was mechanically stirred and heated to 150° C. under a nitrogen atmosphere. Fifteen (15.0) grams of molten N-phenyl-m-toluidine was added dropwise at this temperature. After addition, the resulting mixture was heated at 210° C. under reflux for 24 hours. The hot reaction mixture was filtered, and the filter cake was washed several times with hot cyclohexane. The combined filtrate was evaporated under reduced pressure to give a brown residue which was purified by column chromatography on silica gel to afford 15.2 grams of pure 2,7-bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]-fluorene, melting point 159° to 160° C.

Provenance & Evidence