Methyl iodide → trimethyl{4-[(trimethylsilyl)oxy]phenyl}silane

HRID 434395

Reaction equation

HRID 434395 reaction equation
[Mg].CI.Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=1.Cl[Si:17]([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[CH3:18][Si:17]([CH3:20])([CH3:19])[C:5]1[CH:10]=[CH:9][C:8]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6397ChlorotrimethylsilaneHCID 873501-Bromo-4-((trimethylsilyl)oxy)benzeneHCID 5462224Magnesium

Product 1

HCID 262890trimethyl{4-[(trimethylsilyl)oxy]phenyl}silaneYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.35 g (0.22 mole) magnesium was added to 10 ml tetrahydrofuran and 0.35 ml CH3I under N2 and heated to initiate the Grignard reaction. A solution of 49.0 g (0.2 mole) p-bromophenyoxytrimethylsilane and 63 ml tetrahydrofuran was added over a 11/2 hour period. The reaction mixture was refluxed one additional hour and then cooled to room temperature. 22.8 g (0.21 mole) chlorotrimethylsilane was added to the reaction mixture. Once again the mixture was refluxed 1 hour and then cooled. 100 ml distilled water was slowly added, stirred, and separated. The organic phase was washed with two 50 ml portions of water and finally 50 ml of brine. The organic solution was dried over magnesium sulfate, filtered, and the solvent removed on a rotary evaporator under reduced pressure. Vacuum distillation gave 28.7 g of p-trimethylsilylphenoxytrimethylsilane, bp 132 degrees Celsius at 27 mm Hg.

Workup

  1. temperatureheated
  2. customthe Grignard reaction
  3. temperatureThe reaction mixture was refluxed one additional hour
  4. temperatureOnce again the mixture was refluxed 1 hour
  5. temperaturecooled
  6. distillation100 ml distilled water
  7. additionwas slowly added
  8. customseparated
  9. washThe organic phase was washed with two 50 ml portions of water and finally 50 ml of brine
  10. dry with materialThe organic solution was dried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed on a rotary evaporator under reduced pressure
  13. distillationVacuum distillation

Sources & evidence

ORD record
ord-c978f15b4ae14abdb51962b800d2cbd6
Source dataset
uspto-grants-1983_08
Patent number
US04396704

Linked notes

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