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19th August 2013 @ 14:15

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Reaction information

*#Reaction file
*Reaction file type CDX
*Procedure A 50 mL Schlenk flask containing (2-(4-Bromophenylthio)ethyl)trimethylsilane (534 mg, 1.84 mmol), PdCl2 (16 mg, 0.09 mmol, 5 mol%), PPh3 (48 mg, 0.18 mmol,  10 mol%) and CuI (35 mg, 0.18 mmol, 10 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (20 mL). TEA (0.77 mL, 559 mg, 5.52 mmol, 3.00 eq.) was then added, followed by TMSA (0.31 mL, 217 mg, 2.21 mmol, 1.20 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 22 h; it was stopped before the disappearance of starting material (Rf 0.25, hexane) because the yield of product was not increasing and a byproduct was forming (GC). The solvent was evaporated, the residue was dissolved in DCM and filtered through Celite 521; the solution was then washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude title compound (628 mg). The pure product (164 mg, 0.53 mmol, yield 29%) was obtained by column chromatography on silica gel using as eluent first hexane and then (20/1) hexane/DCM (Rf 0.12 in hexane).
*Yield (%) 29 %
*Type of Yield Isolated pure product
PhD Thesis - 16Sep2010_final p16.pdf
PhD Thesis - 16Sep2010_final p123.pdf
Further information Compound 31: (2-(Trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane

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 Reaction 30: Protection of thiol with alkylsilane: (2-(4-bromophenylthio)ethyl)trimethylsilane
For step in multistep reaction - link to following reaction step Reaction 32: Deprotection of (2-(Trimethylsilyl)ethyl)(4-(2-(trimethylsilyl)ethynyl)phenyl)sulfane: (2-(4-ethynylphenylthio)ethyl)trimethylsilane
Attached Files
PhD Thesis - 16Sep2010_final p123.pdf
PhD Thesis - 16Sep2010_final p16.pdf