(4-Bromobutyl)(ethoxy)dimethylsilane → (4-Bromobutyl)(ethenyl)dimethylsilane

HRID 730250Notes

Reaction equation

HRID 730250 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:15])([CH3:14])OCC>O1CCCC1>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:15])([CH3:14])[CH:1]=[CH2:2]

Participants

4

Reactant 2

HCID 22928485(4-Bromobutyl)(ethoxy)dimethylsilaneHCID 178418507HCID 178418507, compound

Product 1

HCID 22928484(4-Bromobutyl)(ethenyl)dimethylsilaneYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A 3 l reactor was charged under nitrogen with 11 of vinyl magnesium bromide in THF (tetrahydrofuran) and 184 g of 4-bromobutyl-dimethyl-ethoxysilane were added slowly at room temperature. The mixture was then refluxed at 70° C. for 16 h. After cooling on ice, the mixture was quenched with 407 g of a 20% HBr (w/w) solution, after which it was stirred for another 1.5 h. The THF layers were separated from the aqueous layers and neutralized with aq. sodium hydrogen carbonate solution. The THF was evaporated and the residue was distilled in the presence of 1 g Pt/C to obtain 135.8 g (79.8%) of pure 4-bromobutyl-dimethyl-vinylsilane

Workup

  1. additionwere added slowly at room temperature
  2. temperatureAfter cooling on ice
  3. customthe mixture was quenched with 407 g of a 20% HBr (w/w) solution
  4. customThe THF layers were separated from the aqueous layers
  5. customThe THF was evaporated
  6. distillationthe residue was distilled in the presence of 1 g Pt/C

Sources & evidence

ORD record
ord-e7def45522da438c8c81ccfa00ba67b2
Source dataset
uspto-grants-2009_09
Patent number
US07582703B2

Reaction notes

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