Ethane → (4-Bromophenylethynyl)trimethylsilane

HRID 1165755Notes

Reaction equation

HRID 1165755 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.[Mg].CC.Cl[Si:14]([CH3:17])([CH3:16])[CH3:15].[NH4+].[Cl-]>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 6324EthaneHCID 6397ChlorotrimethylsilaneHCID 25517Ammonium ChlorideHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 5462224Magnesium

Product 1

HCID 4226980(4-Bromophenylethynyl)trimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dropwise over 30 minutes, 26.4 g of p-bromophenyl acetylene in solution in 100 ml of tetrahydrofuran were added to 215 ml of the magnesium compound solution prepared above and the reaction was lively and immediately was accompanied by an evolution of ethane and a rise in temperature. The temperature was brought back to 15°-20° C. and stirring was continued for 10 minutes. Over 5 minutes, 20 ml of chlorotrimethylsilane was added dropwise and after allowing the temperature to return to the ambient and stirring for 30 minutes, the reaction medium was diluted by the addition of 200 ml of a saturated aqueous solution of NH4Cl, followed by decanting and extracting with tetrahydrofuran. The extracts were washed with salted water, dried and concentrated to dryness by distilling under reduced pressure. The oily residue was taken up in 150 ml of methanol and crystallization was initated. The crystals were separated, washed and dried to obtain 18.67 g of p-bromophenylethynyl trimethylsilane melting at about 65° C.

Workup

  1. customprepared above and the reaction
  2. customwas brought back to 15°-20° C.
  3. waitwas continued for 10 minutes
  4. waitOver 5 minutes
  5. stirringstirring for 30 minutes
  6. customby decanting
  7. extractionextracting with tetrahydrofuran
  8. washThe extracts were washed with salted water
  9. customdried
  10. concentrationconcentrated to dryness
  11. distillationby distilling under reduced pressure
  12. customcrystallization
  13. customThe crystals were separated
  14. washwashed
  15. customdried

Sources & evidence

ORD record
ord-fab28c40da1d4ce38d2264377c629f31
Source dataset
uspto-grants-1990_03
Patent number
US04912097

Reaction notes

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