9,9-Dichloro-9-silafluorene → 4-(3',5'-Bis-[t-butyl]phenyl)2-isopropylindene

HRID 844456Notes

Reaction equation

HRID 844456 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]([CH:39]([CH3:41])[CH3:40])[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]([CH:39]([CH3:41])[CH3:40])[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 69683378Lithium 4-(3',5'-di-t-butylphenyl)-2-isopropylindene

Product 1

HCID 220230714-(3',5'-Bis-[t-butyl]phenyl)2-isopropylindene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9,9-Dichloro-9-silafluorene (1.1 g, 8.5 mmol) was dissolved in 80 mL of THF. To this solution was slowly added lithium 4-(3′,5′-di-t-butylphenyl)-2-isopropylindene (3.0 g, 8.5 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 as filtered through frit to remove LiCl and the solvent was removed in vacuo and used as a crude product (3.9 g) for the next step.

Workup

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

Sources & evidence

ORD record
ord-a07a477d73be4be1ad8eea91b7eb30b0
Source dataset
uspto-grants-2002_04
Patent number
US06380334B1

Reaction notes

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