Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilane → bis[4-(2,4,6-trimethylphenyl)-2-methyl-1H-inden-1-yl](dimethyl)silane

HRID 605026Notes

Reaction equation

HRID 605026 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.Br[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:36])[CH:17]2[Si:22]([CH:25]1[C:33]2[C:28](=[C:29](Br)[CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[CH3:35])([CH3:24])[CH3:23]>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>[CH3:11][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[C:16]([CH3:36])[CH:17]2[Si:22]([CH:25]1[C:33]2[C:28](=[C:29]([C:2]3[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=3[CH3:11])[CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1[CH3:35])([CH3:24])[CH3:23]

Participants

6

Reactant 2

HCID 59832509Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilaneHCID 178425415HCID 178425415, compound

Product 1

HCID 58897775bis[4-(2,4,6-trimethylphenyl)-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 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF. 13.0 ml of 1.0 M mesitylmagnesium bromide (13.0 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.51 g (5.0 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 2.60 g (94%) 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-b750c6f6480e4c46b8e4d4beea6eb83d
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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