Fluorene → 1,2-Bis(fluorenyl)ethane

HRID 1080832Notes

Reaction equation

HRID 1080832 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].Br[CH2:20][CH2:21]Br>CCOCC>[C:1]1([CH:16]([C:15]2[C:14]3[CH2:21][C:20]4[C:3](=[CH:2][CH:1]=[CH:13][CH:12]=4)[C:4]=3[CH:5]=[CH:6][CH:7]=2)[CH3:17])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:17][CH2:16][C:15]2[C:14]3[CH2:21][C:20]4[C:3](=[CH:2][CH:1]=[CH:13][CH:12]=4)[C:4]=3[CH:5]=[CH:6][CH:7]=2)[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6853FluoreneHCID 78391,2-DibromoethaneHCID 178418339Butyllithium

Product 2

HCID 178250291,2-Bis(fluorenyl)ethaneHCID 19692123Bis(fluorenyl)ethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The ligand bis(fluorenyl)ethane was prepared as follows. To 0.2 mole fluorene in 200 mL ether was added 0.2 mole butyllithium (1.6 M in hexane) at a rate of 0.15 mL/min. at room temperature. The reaction mixture was stirred for one hour, and 0.1 mole 1,2 dibromoethane was added slowly and stirred for 3 hours. The volume was reduced to 150 mL, filtered and the pale yellow solid was washed 2 times with 50 mL distilled water. The pale yellow solid was dried and washed with 100 mL of pentane to yield white 1,2-bis(fluorenyl)ethane. The yield was 80%.

Workup

  1. stirringstirred for 3 hours
  2. filtrationfiltered
  3. washthe pale yellow solid was washed 2 times with 50 mL
  4. distillationdistilled water
  5. customThe pale yellow solid was dried
  6. washwashed with 100 mL of pentane

Sources & evidence

ORD record
ord-f4f29d027fb74c1b831b1e1a5f65321e
Source dataset
uspto-grants-1996_12
Patent number
US05583189

Reaction notes

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