Chlorotrimethylsilane → (2,2-Dichloro-1-methoxy-vinyloxy)-trimethylsilane

HRID 1676515Notes

Reaction equation

HRID 1676515 reaction equation
BrCCBr.[Cl:5][C:6]([Cl:12])(Cl)[C:7]([O:9][CH3:10])=[O:8].[CH3:13][Si:14](Cl)([CH3:16])[CH3:15]>O1CCCC1.CCCCCC.[Zn]>[Cl:5][C:6]([Cl:12])=[C:7]([O:9][CH3:10])[O:8][Si:14]([CH3:16])([CH3:15])[CH3:13]

Participants

7

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 11739Methyl trichloroacetate

Product 1

HCID 11435856(2,2-Dichloro-1-methoxy-vinyloxy)-trimethylsilaneYield 62%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a suspension of 5.9 g (0.091 g-atom) of zinc powder (−325 mesh) in 40 mL of tetrahydrofuran was added 0.2 mL of 1,2-dibromoethane. The mixture was heated at gentle reflux for 30 minutes. The mixture was cooled to room temperature and 7.1 mL (0.06 mole) of methyl trichloroacetate was added dropwise, followed by 9.1 mL (0.097 mole) of trimethylsilyl chloride at rate such the internal temperature was below 50 degrees. The mixture was stirred at room temperature for 1 hour and then diluted with hexane. The resulting solid was removed by filtration, and the filtrate concentrated under reduced pressure. Solids were removed by filtration, washing with hexane. The filtrated was concentrated under reduced pressure and the residue was then distilled under vacuum to give 8.0 g of (2,2-dichloro-1-methoxy-vinyloxy)-trimethyl-silane as a colorless oil. Bp 45-48 degrees at 1 mm Hg.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat gentle reflux for 30 minutes
  3. customwas below 50 degrees
  4. customThe resulting solid was removed by filtration
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customSolids were removed by filtration
  7. washwashing with hexane
  8. concentrationThe filtrated was concentrated under reduced pressure
  9. distillationthe residue was then distilled under vacuum

Sources & evidence

ORD record
ord-ebc598328dd245cda27f13e25799eab7
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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