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

HRID 2417351Notes

Reaction equation

HRID 2417351 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-6ba349bf9b42429d90229bc18d72feff
Source dataset
uspto-grants-2004_11
Patent number
US06825372B2

Reaction notes

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