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23rd August 2013 @ 14:26

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Reaction information

*#Reaction file
reactionscheme_16 .cdx
*Reaction file type CDX
*Procedure A small Schlenk tube containing 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl) benzene(40 mg, 46 μmol), 4-bromobenzonitrile (20 mg, 0.11 mmol, 2.40 eq.), PdCl2 (1 mg, 5.00 μmol, 10 mol%), PPh3 (3 mg, 0.01 mmol, 20 mol%) and CuI (2 mg, 0.01 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding benzene (1.0 mL: ~ 20 mL/mmol) and triethylamine, TEA (0.04 mL, 28 mg, 0.28 mmol, 6.00 eq.) dropwise. The reaction mixture was heated to 70 °C and stirred for 22 h. The solvent was evaporated and the residue was dissolved in DCM; the solution was washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude product (mostly yellow solid, 91 mg). The pure title compound (Rf 0.36; yellow solid, 18 mg, 17 μmol, yield 37%) was obtained by column chromatography on silica gel using as eluent (2/1) DCM/hexane.
*Yield (%) 37 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p13.pdf
PhD Thesis - 16Sep2010_final p114.pdf
Further information Compound 16: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-(2-(p-benzonitril)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 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

Overall reaction 4: 1-acetylthio-4-iodobenzene

For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p114.pdf
reactionscheme_16 .cdx