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

HRID 843194Notes

Reaction equation

HRID 843194 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-1cb33b7c87104b8e9d1a4a21a1f5e253
Source dataset
uspto-grants-2002_04
Patent number
US06376627B1

Reaction notes

Loading…