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28th August 2013 @ 13:57

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Reaction information

*#Reaction file
reactionscheme_22 .cdx
*Reaction file type CDX
*Procedure A 50 mL Schlenk flask containing impure Trimethyl(2-(4-(methylthio)phenyl)ethynyl)silane (541 mg; at least 2.45 mmol of the title compound), 1-bromo-4-iodobenzene (764 mg, 2.70 mmol, 1.10 eq.), PdCl2 (43 mg, 0.24 mmol, 10 mol%), PPh3 (126 mg, 0.48 mmol, 20 mol%) and CuI (46 mg, 0.24 mmol, 10 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (25 mL). 1,8-Diazabicycloundec-7-ene, DBU (4.40 mL, 4.48 g, 29.4 mmol, 12.00 eq.) was then added dropwise, followed by distilled water (~ 0.04 mL, 35 mg, 1.96 mmol, 0.80 eq.). The reaction mixture was heated to 70 ºC and stirred for 1 d, the disappearance of starting material was monitored by TLC (Rf 0.28, (6/1) hexane/DCM). The solvent was evaporated and the solid was dissolved in DCM, the solution was washed with water and brine and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude product (2.137 g) that was column chromatographed on silica gel, using as eluent (3/1) hexane/DCM (Rf 0.31), to obtain the pure product (yellowish flakes (558 mg, 1.84 mmol, yield 75%).
*Yield (%) 75 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p117-118.pdf
Further information Compound 22: 2-(4-(2-(4-bromophenyl)ethynyl)phenyl)methylthioether

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 21: Sonogashira Coupling: trimethyl(2-(4-(methylthio)phenyl)ethynyl)silane
For step in multistep reaction - link to following reaction step Reaction 23: Sonogashira Coupling: trimethyl(2-(4-(2-(4-(methylthio)phenyl)ethynyl)phenyl)ethynyl)silane
Attached Files
reactionscheme_22 .cdx
PhD Thesis - 16Sep2010_final p117-118.pdf