Chlorotrimethylsilane → Trimethyl(M-tolyl)silane

HRID 1265946Notes

Reaction equation

HRID 1265946 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH3:10][Si:11]([CH3:14])([CH3:13])Cl>BrCCBr.C1COCC1>[CH3:10][Si:11]([CH3:14])([CH3:13])[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 79313-ChlorotolueneHCID 5462224Magnesium

Product 1

HCID 10866684Trimethyl(M-tolyl)silaneYield 89.5%

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of m-chlorotoluene (25.3 g, 0.20 mol), 1,2-dibromoethane (2.18 g, 11.6 mmol) and THF (40 cm3) was added to magnesium turnings (5.35 g, 0.22 mol). The mixture was heated under reflux in an atmosphere of argon for 4 h, after which the heating bath was removed and trimethylchlorosilane (23.9 g, 0.22 mol) was added so that gently reflux was maintained. The mixture was stirred for another 30 min and then separated between 5% NaHCO3 (100 cm3) and dichloromethane (3×100 cm3). The organic extract was washed with brine and dried (MgSO4). The solvent was removed under reduced pressure affording the title compound (29.4 g, 89%) as a pale yellow liquid, which was used without purification in the next reaction. All spectroscopic data were identical to those reported in the literature (Eisenhut et al., ibid).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an atmosphere of argon for 4 h
  3. customafter which the heating bath was removed
  4. temperaturethat gently reflux
  5. temperaturewas maintained
  6. customseparated between 5% NaHCO3 (100 cm3) and dichloromethane (3×100 cm3)
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-12bd176b7ec046e78a0e2065f443ab51
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

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