Fluorene → HCID 178435159, compound

HRID 1779560Notes

Reaction equation

HRID 1779560 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.CCCCCC.C([Li])CCC.[Cl-:25].[Cl-].[CH3:27][C:28]1([Zr+2:33][C:34]2([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35]2)[CH:32]=[CH:31][CH:30]=[CH:29]1>C(OCC)C>[Cl-:25].[CH3:27][C:28]1([Zr+:33]([C:34]2([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35]2)[C:1]2[C:13]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)[CH:29]=[CH:30][CH:31]=[CH:32]1

Participants

6

Reactant 4

HCID 6853FluoreneHCID 8058HexaneHCID 178418339ButyllithiumHCID 178435158HCID 178435158, compound

Product 1

HCID 178435159HCID 178435159, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

About 2.4 mmol of fluorene was dissolved in 50 ml of diethylether and mixed with 1.5 ml of a 1.6M hexane solution of butyllithium and stirred for 2 hrs at room temperature. Then 0.77 g of bis(methylcyclopentadienyl) zirconium dichloride was added. The reaction mixture was then stirred for an addition 90 mins. Then the solvent was removed using a vacuum. The residue was extracted with toluene and a suspension filtered over sodium sulfate. The filtrate was freed from solvent and taken up in 50 ml of diethylether. Crystallization at -30° C. yields the product bis(methylcyclopentadienyl) (fluorenyl) zirconium chloride, referred to hereinafter as Catalyst No. 79. The x-ray analysis of the solid Catalyst No. 79 is believed to demonstrate that the fluorenyl is a σ-bound ligand rather than a π-bound ligand.

Workup

  1. stirringThe reaction mixture was then stirred for an addition 90 mins
  2. customThen the solvent was removed
  3. extractionThe residue was extracted with toluene
  4. filtrationa suspension filtered over sodium sulfate
  5. customCrystallization at -30° C.

Sources & evidence

ORD record
ord-7bfdf0d1f7754999881850028918d657
Source dataset
uspto-grants-1997_05
Patent number
US05627247

Reaction notes

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