9,9-Dichloro-9-silafluorene → 4-(3',5'-Di-t-butylphenyl)-2-methylindene

HRID 844462Notes

Reaction equation

HRID 844462 reaction equation
Cl[Si]1(Cl)C2C=CC=CC=2C2C1=CC=CC=2.[C:16]([C:20]1[CH:21]=[C:22]([C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2[CH:32]=[C:33]([CH3:39])[CH2:34]3)[CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=1)([CH3:19])([CH3:18])[CH3:17].[Li]>C1COCC1>[C:16]([C:20]1[CH:21]=[C:22]([C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2[CH:32]=[C:33]([CH3:39])[CH2:34]3)[CH:23]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=1)([CH3:17])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 6195839,9-Dichloro-9-silafluoreneHCID 69684158Lithium 4(3',5'-di-t-butylphenyl)-2-methylindene

Product 1

HCID 120107434-(3',5'-Di-t-butylphenyl)-2-methylindene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9,9-Dichloro-9-silafluorene (1.2 g, 9.2 mmol) was dissolved in 80 mL of THF. To this solution was slowly added lithium 4-(3′,5′-di-t-butylphenyl)-2-methylindene (3.0 g, 9.2 mmol) as a dry powder and the solution was stirred overnight. After this time, the solvent was removed in vacuo and the residue was taken up in diethyl ether. The solution was filtered through a frit to remove LiCl and the solvent was removed in vacuo and used as a crude product (4.1 g) for the next step.

Workup

  1. customAfter this time, the solvent was removed in vacuo
  2. filtrationThe solution was filtered through a frit
  3. customto remove LiCl
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bfca49cb1cdf44218af5377ad40134d7
Source dataset
uspto-grants-2002_04
Patent number
US06380330B1

Reaction notes

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