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28th August 2013 @ 14:04

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Reaction information

*#Reaction file
reactionscheme_23 .cdx
*Reaction file type CDX
*Procedure A 100 mL Schlenk flask containing 2-(4-(2-(4-Bromophenyl)ethynyl)phenyl)methylthioether (547 mg, 1.80 mmol), PdCl2 (16 mg, 0.09 mmol, 5 mol%), PPh3 (47 mg, 0.18 mmol, 10 mol%) and CuI (17 mg, 0.09 mmol, 5 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (18 mL). triethylamine, TEA (0.75 mL, 546 mg, 5.40 mmol, 3.00 eq.) was then added, followed by TMSA (0.30 mL, 212 mg, 2.16 mmol, 1.20 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 21 h; the disappearance of starting material (Rf 0.31, (3/1) hexane/DCM) was monitored by TLC. The solvent was evaporated and the residual dissolved in DCM; the solution was filtered through Celite521, washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude title compound (640 mg). The pure product (yellowish solid, 418 mg, 1.30 mmol, yield 72%) was obtained by column chromatography on silica gel, with eluent (10/1) hexane/DCM (Rf 0.16).
*Yield (%) 72 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p118.pdf
Further information Compound 23: trimethyl(2-(4-(2-(4-(methylthio)phenyl)ethynyl)phenyl)ethynyl)silane

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 22: Sonogashira Coupling: 2-(4-(2-(4-bromophenyl)ethynyl)phenyl)methylthioether
For step in multistep reaction - link to following reaction step Reaction 24: Deprotection of TMS group: 2-(4-(2-(4-(methylthio)phenyl)ethynyl)phenyl)ethynylene
Attached Files
reactionscheme_23 .cdx
PhD Thesis - 16Sep2010_final p118.pdf