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23rd August 2013 @ 14:12

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Reaction information

*#Reaction file
reactionscheme_14 .cdx
*Reaction file type CDX
*Procedure A 25 mL Schlenk flask containing 1,4-didodecyl-2,5-bis(2-(4-(2-(4-bromophenyl)ethynyl)phenyl)ethynyl)-benzene (191 mg, 0.20 mmol), PdCl2 (4 mg, 0.02 mmol, 10 mol%), PPh3 (11 mg, 0.04 mmol, 20 mol%) and CuI (8 mg, 0.04 mmol, 20 mol%), with stirring, was evacuated under high vacuum and refilled with Ar before adding distilled benzene (10 mL: five time excess than in the usual procedure). Trimethylamine, TEA (0.16 mL, 122 mg, 1.20 mmol, 6.00 eq.) was then added, followed by trimethylsilylacetylene, TMSA (0.06 mL, 47 mg, 0.48 mmol, 2.40 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 17 h; the disappearance of starting material (Rf 0.05, hexane) was monitored by TLC. The solvent was evaporated, the residue was dissolved in DCM and filtered through Celite521; the solution was then washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude title compound (250 mg). The pure product (white solid, 61 mg, 0.06 mmol, yield 30%) was obtained by column chromatography on silica gel, with eluent (6/1) hexane/DCM (Rf 0.33).
*Yield (%) 30 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p13.pdf
PhD Thesis - 16Sep2010_final p112-113.pdf
Further information Compound 14: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)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 13: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-bromophenyl)ethynyl)phenyl)ethynyl)-benzene
For step in multistep reaction - link to following reaction step Reaction 15: Deprotection of 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene
Attached Files
PhD Thesis - 16Sep2010_final p112-113.pdf
reactionscheme_14 .cdx