Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilane → bis[4-(3-trifluoromethylphenyl)-2-methyl-1H-inden-1-yl](dimethyl)silane

HRID 605027Notes

Reaction equation

HRID 605027 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.Br[C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[C:17]([CH3:37])[CH:18]2[Si:23]([CH:26]1[C:34]2[C:29](=[C:30](Br)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[CH3:36])([CH3:25])[CH3:24]>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>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([CH3:37])[CH:18]3[Si:23]([CH:26]2[C:34]3[C:29](=[C:30]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:12])([F:11])[F:1])[CH:8]=4)[CH:31]=[CH:32][CH:33]=3)[CH:28]=[C:27]2[CH3:36])([CH3:25])[CH3:24])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 59832509Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilaneHCID 178506173HCID 178506173, compound

Product 1

HCID 58897762bis[4-(3-trifluoromethylphenyl)-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 28.0 ml of 15 mL of THF with 0.5 M ZnCl2 (14.0 mmol) in THF, 12.3 ml of 1.02 M 3-trifluoromethylphenylmagnesium bromide (12.6 mmol) in THF was added at ambient temperature. This mixture was stirred for 1 hour, and, then, 9.66 ml of 0.02 M Pd(PtBu3)2 (0.19 mmol, 4 mol. %) in THF and 2.42 g (4.83 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 2.86 g (98%) 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-69344f60c9a84019951f7a27eaf00ce5
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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