9,9-Bis(3,5-dibromophenyl)fluorene → 12,12-Bis(3,5-dibromophenyl)-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene

Participants

Reaction Conditions

Reaction Steps

24.0 ml (60 mmol) of n-butyllithium (2.5 N in hexane) are added dropwise to a solution, cooled to −78° C., of 23.9 g (60 mmol) of 3-(2-bromophenyl)-N-phenylcarbazole in 500 ml of THF, the mixture is subsequently stirred at −78° C. for a further 30 min., and a solution of 38.0 g (60 mmol) of 9,9-bis-(3,5-dibromophenyl)fluorene in 100 ml of THF is then added dropwise. When the addition is complete, the mixture is allowed to warm to room temperature, the THF is removed in vacuo, the residue is taken up in 500 ml of glacial acetic acid, 5 ml of hydrogen bromide are added, and the suspension is heated under reflux for half an hour. After cooling, the solid is filtered off with suction, washed three times with 300 ml of ethanol and recrystallised once from toluene/ethanol. Yield: 36.2 g (45 mmol), 75.3%, purity about 97% (HPLC).

Provenance & Evidence