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

HRID 842482Notes

Reaction equation

HRID 842482 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 LiC 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 LiC
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1d9e73d314d94b9cabf6525ff6e8b898
Source dataset
uspto-grants-2002_04
Patent number
US06376412B1

Reaction notes

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