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23rd August 2013 @ 13:07

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Reaction information

*#Reaction file
reactionscheme_12 .cdx
*Reaction file type CDX
*Procedure A 25 mL Schlenk flask containing 1-(2-(2,5-Didodecyl-4-(2-(4-ethynylphenyl)ethynyl)phenyl)ethynyl)-4-ethynylbenzene(580 mg, 0.79 mmol), 1-Acetylthio-4-iodobenzene (484 mg, 1.74 mmol, 2.20 eq.), PdCl2 (14 mg, 0.08 mmol, 10 mol%), PPh3 (41 mg, 0.16 mmol, 20 mol%) and CuI (30 mg, 0.16 mmol, 2 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled THF (10 mL) and Ethyldiisopropylamine, EDIA (0.82 mL, 613 mg, 4.74 mmol, 6.00 eq.) dropwise. The reaction mixture was stirred at r.t. for 4 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 organic phases were joined, dried over anhydrous MgSO4 and vacuum evaporated. The crude product (975 mg) was column chromatographed on silica gel, using as eluent (1/1) hexane/DCM (Rf0.31), to afford the pure product (yellowish solid, 549 mg, 0.53 mmol, yield 67%).
*Yield (%) 67 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
PhD Thesis - 16Sep2010_final p111.pdf
Further information Compound 12: 1,4-didodecyl-2,5-(2-(4-(2-(4-thioacetylphenyl)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

Overall reaction 4: 1-acetylthio-4-iodobenzene

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 p111.pdf
reactionscheme_12 .cdx