Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilane → bis[4-(4-methylphenyl)-2-methyl-1H-inden-1-yl] (dimethyl)silane

HRID 605025Notes

Reaction equation

HRID 605025 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.Br[C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([CH3:34])[CH:15]2[Si:20]([CH:23]1[C:31]2[C:26](=[C:27](Br)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[CH3:33])([CH3:22])[CH3:21]>C1COCC1.[Cl-].[Cl-].[Zn+2].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:9][C:1]1[CH:6]=[CH:5][C:4]([C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH:13]=[C:14]([CH3:34])[CH:15]3[Si:20]([CH:23]2[C:31]3[C:26](=[C:27]([C:4]4[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=4)[CH:28]=[CH:29][CH:30]=3)[CH:25]=[C:24]2[CH3:33])([CH3:22])[CH3:21])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 59832509Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilaneHCID 178418370HCID 178418370, compound

Product 1

HCID 12162319bis[4-(4-methylphenyl)-2-methyl-1H-inden-1-yl] (dimethyl)silane

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

In an argon atmosphere, to a solution of 15 mL of THF with 34.0 ml of 0.5 M ZnCl2 (17.0 mmol) in THF, 15.2 ml of 1.0 M p-tolylmagnesium bromide (15.2 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 11.7 ml of 0.02 M Pd(PtBu3)2 (0.23 mmol, 4 mol. %) in THF and 2.78 g (5.86 mmol) of 1 were added. The resulting mixture was stirred for 5 hours at reflux. The product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes). Yield 2.79 g (96%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.

Workup

  1. stirringThe resulting mixture was stirred for 5 hours
  2. temperatureat reflux
  3. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 μm, d 30 mm, l 100 mm; eluent: hexanes)

Sources & evidence

ORD record
ord-9a61a6e1bcfd4878a8d26a52ea20bd05
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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