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Dichlorodimethylsilane → HCID 178427960, compound

HRID 585176
Notes
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Reaction equation

HRID 585176 reaction equation
[Mg].[Cl:2][C:3]1[CH:4]([SiH](C)C)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Br[C:16]1CC2C(C=1)=CC=CC=2.Cl[Si:26](Cl)([CH3:28])C>O1CCCC1>[Cl:2][C:3]1[CH:28]([SiH3:26])[C:6]2[C:5]([C:4]=1[CH3:16])=[C:10]([CH3:11])[CH:9]=[CH:8][CH:7]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6398DichlorodimethylsilaneHCID 5755861H-Indene, 2-bromo-HCID 5462224Magnesium2×HCID 178504339HCID 178504339, compound

Product 1

HCID 178427960HCID 178427960, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Under nitrogen flow, 50 ml of THF (tetrahydrofuran) and 2.5 g (41 mmol) of magnesium was placed in a 1 liter 3-necked flask, to which 0.1 ml of 1 2-dibromoethane was added and stirred for 30 minutes to activate magnesium. After stirring, solvent was withdrawn and 50 ml of THF was newly added. To this, 5.0 g (25.6 mmol) of 2-bromoindene in THE (200 ml) solution was dropped in 2 hours. Then the solution was stirred at room temperature for 2 hours and cooled down to −78 ° C., to which 3.1 ml (25.6 mmol) of dichlorodimethylsilane in THF (100 ml) solution was dropped in one hour, followed by stirring for 15 hours and the solvent was distilled off. The residue was extracted by 200 ml of hexane and by distilling off the solvent, 6.6 g (24.2 mmol) of 2-chloro-dimethyl-silylindene was obtained (yield 94%).

Workup

  1. additionwas added
  2. stirringAfter stirring
  3. customsolvent was withdrawn
  4. addition50 ml of THF was newly added
  5. stirringThen the solution was stirred at room temperature for 2 hours
  6. additionwas dropped in one hour
  7. stirringby stirring for 15 hours
  8. distillationthe solvent was distilled off
  9. extractionThe residue was extracted by 200 ml of hexane
  10. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-1c779a3f7f554fe7ad7f9bc17d99f7b1
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06930160B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes