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

HRID 1808691Notes

Reaction equation

HRID 1808691 reaction equation
C([Li])CCC.BrC1C=CC=CC=1[C:13]1[CH:14]=[CH:15][C:16]2[N:17](C3C=CC=CC=3)[C:18]3[C:23]([C:24]=2[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3.[Br:32][C:33]1[CH:34]=[C:35]([C:40]2([C:53]3[CH:58]=[C:57]([Br:59])[CH:56]=[C:55]([Br:60])[CH:54]=3)[C:52]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:46]3[C:41]2=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:36]=[C:37]([Br:39])[CH:38]=1>C1COCC1>[Br:32][C:33]1[CH:34]=[C:35]([C:40]2([C:53]3[CH:58]=[C:57]([Br:59])[CH:56]=[C:55]([Br:60])[CH:54]=3)[C:52]3=[CH:51][C:50]4[N:17]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:16]5[C:15]([C:49]=4[CH:48]=[C:47]3[C:46]3[C:41]2=[CH:42][CH:43]=[CH:44][CH:45]=3)=[CH:14][CH:13]=[CH:25][CH:24]=5)[CH:36]=[C:37]([Br:39])[CH:38]=1

Participants

5

Reactant 3

HCID 461918289,9-Bis(3,5-dibromophenyl)fluoreneHCID 669295403-(2-Bromophenyl)-9-phenyl-9H-carbazoleHCID 178418339Butyllithium

Product 1

HCID 6692986812,12-Bis(3,5-dibromophenyl)-10-phenyl-10,12-dihydro-10-aza-indeno[2,1-b]fluorene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  1. additionWhen the addition
  2. temperatureto warm to room temperature
  3. customthe THF is removed in vacuo
  4. addition5 ml of hydrogen bromide are added
  5. temperaturethe suspension is heated
  6. temperatureunder reflux for half an hour
  7. temperatureAfter cooling
  8. filtrationthe solid is filtered off with suction
  9. washwashed three times with 300 ml of ethanol
  10. customrecrystallised once from toluene/ethanol

Sources & evidence

ORD record
ord-2e626ef0118d43ed8b43f9a4e1be4d7a
Source dataset
uspto-grants-2013_01
Patent number
US08361638B2

Reaction notes

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