Fluorene → 1,1'-(9H-Fluorene-2,7-diyl)bis(4-chlorobutan-1-one)

Participants

Reaction Steps

To a solution of 23.6 g (0.142 mole) of fluorene and 50.0 g (0.35 mole) of 4-chlorobutyryl chloride in 1500 ml of methylene chloride chilled to -20°C., is added 39.8 g (0.298 mole) of aluminum chloride with rapid stirring. The reaction mixture is refluxed for 4 hours, stirred at room temperature for 16 hours and is poured onto an ice/concentrated HCl mixture. The organic layer is separated, washed with saturated sodium bicarbonate solution and dried over magnesium sulfate. The methylene chloride solution is filtered, evaporated to dryness, and the solid residue recrystallized from acetone to yield the desired 2,7-bis(4-chlorobutyryl)fluorene.

Provenance & Evidence