Allyl bromide → Diallyldichlorosilane

HRID 2073916Notes

Reaction equation

HRID 2073916 reaction equation
[Si:1]([Cl:5])(Cl)(Cl)[Cl:2].[CH2:6]([Mg]Br)[CH:7]=[CH2:8].[Mg].[CH2:12](Br)[CH:13]=[CH2:14]>CCOCC>[CH2:6]([Si:1]([CH2:14][CH:13]=[CH2:12])([Cl:5])[Cl:2])[CH:7]=[CH2:8]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24816Silicon tetrachlorideHCID 5462224MagnesiumHCID 178455850HCID 178455850, compound

Product 1

HCID 19288DiallyldichlorosilaneYield 15%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a one-liter 3-neck flask with reflux condenser and dropping funnel, 29 g (170 mmoles) of SiCl4 in 150 mL of anhydrous ether were added. Allyl magnesium bromide solution [from 10 g (400 mmoles) of magnesium and 41.5 g (34 mmoles) of allyl bromide in 250 mL of anhydrous ether], filtered through glass wool, was added dropwise, MgBrCl precipitating. After boiling for 1.5 hours under reflux and washing the residue, diallyldichlorosilane was obtained at 56° C. and 16 hPa as a colorless liquid in a 15% yield.

Workup

  1. temperatureTo a one-liter 3-neck flask with reflux condenser
  2. additionwas added dropwise
  3. temperatureunder reflux
  4. washwashing the residue

Sources & evidence

ORD record
ord-34f9fee240f648418f92dc362aa86631
Source dataset
uspto-grants-1990_04
Patent number
US04920184

Reaction notes

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