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23rd August 2013 @ 08:49

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Reaction information

*#Reaction file
reactionscheme_7 .cdx
*Reaction file type CDX
*Procedure A 250 mL Schlenk flask containing 1,4-didodecyl-2,5-diiodobenzene (6.665 g, 10.00 mmol), PdCl2 (177 mg, 1.00 mmol, 10 mol%), PPh3 (525 mg, 2.00 mmol, 20 mol%) and CuI (381 mg, 1.00 mmol, 10 mol%), with stirring, was evacuated under high vacuum and refilled with Ar before adding distilled benzene (100 mL). Triethylamine,TEA (8.36 mL, 6.071 g, 60.00 mmol, 6.00 eq.) was then added, followed by trimethylsilylacetylene, TMSA (3.39 mL, 2.357 g, 24.00 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 vacuum evaporated and the solid was dissolved in DCM, the solution was washed with water twice and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude title compound (7.298 g) which was column chromatographed on silica gel, using as eluent (20/1) hexane/DCM (Rf0.5), to obtain the pure product (yellowish solid, 3.524 g, 5.80 mmol, yield 58%).
*Yield (%) 58 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
PhD Thesis - 16Sep2010_final p108.pdf
Further information Compound 7: 1,4-Didodecyl-2,5-bis(2-(trimethylsilyl)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 6: Halogenation of 1,4-didodecylbenzene with Iodine: 1,4-didodecyl-2,5-diiodobenzene
For step in multistep reaction - link to following reaction step Reaction 8: Bidirectional Sonogashira Coupling: 1-bromo-4-(2-(4-(2-(4-bromophenyl)ethynyl)-2,5-didodecylphenyl)-ethynyl)benzene
Attached Files
PhD Thesis - 16Sep2010_final p108.pdf
reactionscheme_7 .cdx