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28th August 2013 @ 14:40

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Reaction information

*#Reaction file
reactionscheme_25 .cdx
*Reaction file type CDX
*Procedure A small Schlenk tube containing 1,4-Didodecyl-2,5-diiodobenzene (173 mg, 0.26 mmol), 2-(4-(2-(4-(Methylthio)phenyl)ethynyl)phenyl)ethynylene (144 mg, 0.57 mmol, 2.20 eq.), PdCl2 (5 mg, 26 μmol, 10 mol%), PPh3 (14 mg, 0.05 mmol, 20 mol%) and CuI (10 mg, 0.05 mmol, 20 mol%) was evacuated and refilled with Ar before adding distilled benzene (5.0 mL) and triethylamine, TEA (0.20 mL, 158 mg, 1.56 mmol, 6.00 eq.). The reaction mixture was heated to 70 °C and stirred in the darkness for 16 h; the disappearance of starting materials (Rfs 0.88 and 0.59 respec., (1/1) hexane/DCM) as monitored by TLC was not complete after 13 h: the reaction was not monitored again and assumed stationary because of the presence of at least seven byproducts absorbing light at 365 nm. The solvent was vacuum evaporated, the residue dissolved in DCM, washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, the crude title compound (282 mg). The pure product (110 mg, 0.12 mmol, yield 47%) was obtained by column chromatography on silica gel, using as eluent (2/1) hexane/DCM (Rf 0.50).
*Yield (%) 47 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p119-120.pdf
Further information Compound 25: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-methylthio)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 6: Halogenation of 1,4-didodecylbenzene with Iodine: 1,4-didodecyl-2,5-diiodobenzene

Reaction 24: Deprotection of TMS group: 2-(4-(2-(4-(methylthio)phenyl)ethynyl)phenyl)ethynylene

For step in multistep reaction - link to following reaction step  
Attached Files
reactionscheme_25 .cdx
PhD Thesis - 16Sep2010_final p119-120.pdf