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23rd August 2013 @ 09:44

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Reaction information

*#Reaction file
reactionscheme_11 .cdx
*Reaction file type CDX
*Procedure A 50 mL Schlenk flask containing 1-(2-(2,5-Didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene (687 mg, 1.03 mmol), 4-bromobenzonitrile (415 mg, 2.28 mmol, 2.21 eq.), PdCl2 (18 mg, 0.10 mmol, 10 mol%), PPh3 (54 mg, 0.21 mmol, 20 mol%) and CuI (39 mg, 0.21 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled THF (15 mL). TEA (0.86 mL, 625 mg, 6.18 mmol, 6.00 eq.) was then added dropwise and the reaction mixture was stirred at r.t. for 22 h; the disappearance of starting material (Rf 0.12, hexane) was monitored by TLC. The solvent was evaporated and the residue was dissolved in DCM; the solution was filtered through Celite521, washed with water and brine then dried over anhydrous MgSO4. After evaporation of the solvent, the crude title compound (1.063 g) was column chromatographed on silica gel, using as eluent (2/1) DCM/hexane (Rf 0.36), to afford the product (yellow solid, 367 mg, 0.42 mmol, yield 41%)
*Yield (%) 41 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
 
PhD Thesis - 16Sep2010_final p110-111.pdf
Further information Compound 11: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-cyanophenyl)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 10: Deprotection of TMS group from terminal alkyne: 1-(2-(2,5-didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene
For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p110-111.pdf
reactionscheme_11 .cdx