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23rd August 2013 @ 09:19

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Reaction information

*#Reaction file
reactionscheme_9 .cdx
*Reaction file type CDX
*Procedure A 50 mL Schlenk flask containing 1-bromo-4-(2-(4-(2-(4-bromophenyl)ethynyl)-2,5-didodecylphenyl)-ethynyl)benzene(2.275 g, 2.94 mmol), PdCl2 (51 mg, 0.29 mmol, 10 mol%), PPh3 (155 mg, 0.59 mmol, 20 mol%) and CuI (112 mg, 0.59 mmol, 20 mol%), with stirring, was evacuated under high vacuum and refilled with Ar before adding distilled benzene (30 mL). Triethylamine, TEA (2.46 mL, 1.785 g, 17.64 mmol, 6.00 eq.) was then added, followed by trimethylsilylacetylene, TMSA (1.00 mL, 693 mg, 7.05 mmol, 2.40 eq.) dropwise. The reaction mixture was heated to 70 ºC and stirred in the darkness for 20 h, the disappearance of starting material was monitored by TLC. The solvent was evaporated and the solid was dissolved in DCM, the solution was filtered through Celite 521, washed with water twice and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude product (2.472 g). This was column chromatographed on silica gel, using as eluent (20/1) hexane/DCM (Rf0.19), to obtain the pure title compound (1.613 g, 2.00 mmol, yield 68%).
*Yield (%) 68 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
 
PhD Thesis - 16Sep2010_final p109.pdf
Further information Compound 9: 1,4-didodecyl-2,5-bis(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)-ethynyl)benzene

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 8: Bidirectional Sonogashira Coupling: 1-bromo-4-(2-(4-(2-(4-bromophenyl)ethynyl)-2,5-didodecylphenyl)-ethynyl)benzene
For step in multistep reaction - link to following reaction step Reaction 10: Deprotection of TMS group from terminal alkyne: 1-(2-(2,5-didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene
Attached Files
PhD Thesis - 16Sep2010_final p109.pdf
reactionscheme_9 .cdx