Chlorotrimethylsilane → Trimethyl(M-tolyl)silane

HRID 1265952Notes

Reaction equation

HRID 1265952 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.BrCCBr.[Mg].[CH3:14][Si:15]([CH3:18])([CH3:17])Cl.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:14][Si:15]([CH3:18])([CH3:17])[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 78391,2-DibromoethaneHCID 79313-ChlorotolueneHCID 516892Sodium BicarbonateHCID 5462224Magnesium

Product 1

HCID 10866684Trimethyl(M-tolyl)silaneYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of m-chlorotoluene (12.66 g, 0.100 mol) and 1,2-dibromoethane (0.5 ml) in THF (20 ml) was added to magnesium turnings (2.67 g, 0.110 mol). The mixture was heated under reflux for 4 h, after which the heating bath was removed and trimethylchlorosilane (11.08 g, 0.102 mol) was added so that gentle reflux was maintained. The mixture was stirred for another 0.5 h and 5% NaHCO3 (100 ml) was then added. The resulting mixture was extracted with CH2Cl2 (3×50 ml), the organic phase was washed with brine and dried (MgSO4). Filtration and evaporation provided 15.05g (92%) of 36 as a pale yellow liquid. Spectroscopic data were identical to those previously reported in the literature.40

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h
  3. customafter which the heating bath was removed
  4. temperaturethat gentle reflux
  5. temperaturewas maintained
  6. extractionThe resulting mixture was extracted with CH2Cl2 (3×50 ml)
  7. washthe organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-bfe9f852ba984c97a54e5a941fac1ebb
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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