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28th August 2013 @ 10:16

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Reaction information

*#Reaction file
reactionscheme_20 .cdx
*Reaction file type CDX
*Procedure A 25 mL Schlenk flask containing 1,4-Didodecyl-2,5-diiodobenzene (133 mg, 0.20 mmol), 4-Ethynylbenzonitrile (51 mg, 0.40 mmol, 2.00 eq.), PdCl2 (7 mg, 40 μmol, 20 mol%), PPh3 (21 mg, 80 μmol, 40 mol%) and CuI (8 mg, 40 μmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (5.0 mL) and triethylamine, TEA (0.17 mL, 121 mg, 1.20 mmol, 6.00 eq.). The reaction mixture was heated to 80 ºC and stirred in the darkness for 4.5 h, the disappearance of starting material was monitored by TLC. The solvent was evaporated and the solid was dissolved in DCM and washed with water, the water was extracted three times with DCM, and the combined organic phases were washed again with water before being dried over anhydrous MgSO4and evaporated. The crude product (180 mg) was column chromatographed on silica gel, using as eluent (1/1) hexane/DCM, to afford the pure title compound (58 mg, 0.09 mmol, yield 43%), of which a small fraction (10 mg) was recrystallized from EtOH as tiny white needles. 
*Yield (%) 43 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p116.pdf
Further information Compound 20: 1,4-didodecyl-2,5-bis-(2-(4-cyanobenzil)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

Reaction 19: Deprotection of 4-(2-(trimethylsilyl)ethynyl)benzonitrile: 4-ethynylbenzonitrile

For step in multistep reaction - link to following reaction step  
Attached Files
reactionscheme_20 .cdx