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19th August 2013 @ 13:55

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Reaction information

*#Reaction file
reactionscheme_30 .cdx
*Reaction file type CDX
*Procedure A Schlenk tube  containing 4-bromothiophenol (756 mg, 4.00 mmol) was evacuated and refilled with argon before adding vinyltrimethylsilane (0.67 mL, 461 mg, 4.60 mmol, 1.15 eq.) and tertbutylperoxide (0.11 mL, 88 mg, 0.60 mmol, 0.15 eq.); the mixture was stirred at 100 °C for 3 hours and the disappearance of starting material monitored by GC.  Hexane was poured in the flask and the solution was extracted once with NaOH (5% aq.); after drying over MgSO4 and evaporation of the solvent a mixture of crude title compound and disulfide byproduct was obtained (yellow oil, 814 mg). This was column chromatographed on silica gel using hexane as eluent; once the disulfide (Rf 0.34; white solid) had been separated the pure product (clear oil, 534 mg, 1.85 mmol, yield 46%; Rf 0.26 in hexane ) was recovered eluting with (2/1) hexane/ethylacetate.
*Yield (%) 46 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p16.pdf
 
PhD Thesis - 16Sep2010_final p122.pdf
Further information (2-(4-bromophenylthio)ethyl)trimethylsilane

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step Reaction 31: Sonogashira Coupling: (2-(trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane
Attached Files
PhD Thesis - 16Sep2010_final p16.pdf
PhD Thesis - 16Sep2010_final p122.pdf
reactionscheme_30 .cdx