Benzo(B)Thiophene → bis[4-(1-benzothien-2-yl)-2-methyl-1H-inden-1-yl](dimethyl)silane

HRID 605028Notes

Reaction equation

HRID 605028 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[Li][CH2:11][CH2:12][CH2:13][CH3:14].Br[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[C:19]([CH3:39])[CH:20]2[Si:25]([CH:28]1[C:36]2[C:31](=[C:32](Br)[CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[CH3:38])([CH3:27])[CH3:26]>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>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:16]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:17]=1[CH:18]=[C:19]([CH3:39])[CH:20]2[Si:25]([CH:28]1[C:36]2[C:31](=[C:32]([C:11]3[S:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:14][C:13]=4[CH:12]=3)[CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[CH3:38])([CH3:27])[CH3:26]

Participants

7

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 59832509Bis(4-bromo-2-methyl-1h-inden-1-yl)dimethylsilaneHCID 178418339Butyllithium

Product 1

HCID 58897764bis[4-(1-benzothien-2-yl)-2-methyl-1H-inden-1-yl](dimethyl)silane

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

In an argon atmosphere, to a solution of 1.74 g (13.0 mmol) of benzothiophene in 30 ml of THF, 5.24 ml of 2.5 M nBuLi (13.0 mmol) in hexanes was added at ambient temperature. This mixture was stirred for 2 hours, and, then, 29.0 ml of 0.5 M ZnCl2 (14.5 mmol) in THF was added. The resulting mixture was stirred for 1 hour. Then, 10.0 ml of 0.02 M Pd(PtBu3)2 (0.20 mmol, 4 mol. %) in THF and 2.37 g (5.0 mmol) of 1 were added. This 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 2.76 g (95%) of white solid of ca. 1 to 1 mixture of rac- and meso-compounds.

Workup

  1. stirringThe resulting mixture was stirred for 1 hour
  2. stirringThis mixture was stirred for 5 hours
  3. temperatureat reflux
  4. 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-630e6299a99943aabd12233eef0fe975
Source dataset
uspto-grants-2011_03
Patent number
US07910783B2

Reaction notes

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