HCID 178418348, compound → HCID 92002078, compound

HRID 2297366Notes

Reaction equation

HRID 2297366 reaction equation
[Cl-].[Cl-].[CH2:3]([C:7]1([Zr+2:13]C2(CCCC)C=CC(C)=C2)[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8]1)[CH2:4][CH2:5][CH3:6].[Li][CH3:25]>C1(C)C=CC=CC=1>[CH3-:3].[CH3-:25].[CH3:6][CH2:5][CH2:4][CH2:3][C-:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11]1.[CH3:6][CH2:5][CH2:4][CH2:3][C-:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11]1.[Zr+4:13]

Participants

4

Reactant 2

HCID 178418348HCID 178418348, compoundHCID 178442028HCID 178442028, compound

Product 1

HCID 92002078HCID 92002078, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bis(1-butyl-3-methylcyclopentadienyl)zirconium dichloride (2.71 g, 6.26 mmol) was dissolved in 21.4 g of toluene. Low-halide MeLi (˜1.5 M in ether, 8.0 mL) was added dropwise at ambient temperature. A white solid formed immediately. The reaction was allowed to stir for 1.5 hours. Analysis of the reaction showed 3.5 mol % of mono-methyl intermediate. An additional aliquot of MeLi (0.4 mL) was then added to consume the monomethyl intermediate. After stirring overnight, the supernatant liquid was reanalyzed to verify that the reaction was complete. The slurry was filtered on a medium frit and the solvent was removed in vacuo. A light yellow liquid of bis(1-butyl-3-methyl-cyclopentadienyl)zirconium dimethyl remained (2.13 g, 87% yield).

Workup

  1. additionwas added dropwise at ambient temperature
  2. customA white solid formed immediately
  3. customto consume the monomethyl intermediate
  4. stirringAfter stirring overnight
  5. filtrationThe slurry was filtered on a medium frit
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a59169da0ce44de6a8685c3408250664
Source dataset
uspto-grants-2002_12
Patent number
US06492292B2

Reaction notes

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