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23rd August 2013 @ 09:10

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Reaction information

*#Reaction file
reactionscheme_8 .cdx
*Reaction file type CDX
*Procedure Into a 100 mL Schlenk flask was added 1,4-Didodecyl-2,5-bis(2-(trimethylsilyl)ethynyl)benzene (3.524 g, 5.80 mmol), 1-bromo-4-iodobenzene (3.282 g, 11.60 mmol, 2.00 eq.), PdCl2 (247 mg, 1.39 mmol, 24 mol%), PPh3(730 mg, 2.78 mmol, 48 mol%) and CuI (221 mg, 1.16 mmol, 20 mol%), with stirring. The mixture was evacuated under high vacuum and refilled with Ar before the addition of distilled benzene (50 mL). 1,8-Diazabicycloundec-7-ene, DBU (20.8 mL, 21.19 g, 139.2 mmol, 24.00 eq.) was then added dropwise, followed by distilled water (0.17 mL, 167 mg, 9.28 mmol, 1.60 eq.). The reaction mixture was heated to 70 ºC and stirred in the darkness for 17 h, the disappearance of the starting material was monitored by TLC. The solvent was 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, a dark-brown oil (10.124 g), which was column chromatographed on silica gel, using as eluent (7/1) hexane/DCM (Rf 0.57), to obtain the pure product (yellow solid, 2.342 g, 3.03 mmol, yield 52%).
*Yield (%) 52 %
*Type of Yield Isolated pure product
PhD Thesis - 16Sep2010_final p12.pdf
PhD Thesis - 16Sep2010_final p108-109.pdf
Further information Compound 8: 1-Bromo-4-(2-(4-(2-(4-bromophenyl)ethynyl)-2,5-didodecylphenyl)-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 7: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(trimethylsilyl)ethynyl)benzene
For step in multistep reaction - link to following reaction step Reaction 9: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)-ethynyl)benzene
Attached Files
reactionscheme_8 .cdx
PhD Thesis - 16Sep2010_final p108-109.pdf