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29th August 2013 @ 10:57

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Reaction information

*#Reaction file
reactionscheme_28 .cdx
*Reaction file type CDX
*Procedure A 25 mL Schlenk flask containing 1,4-Diiodo-2,5-bis(octyloxy)benzene (152 mg, 0.26 mmol), 2-(4-(2-(4-(Methylthio)phenyl)ethynyl)phenyl)ethynylene (144 mg, 0.58 mmol, 2.23 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). Triethylamine, TEA (0.20 mL, 158 mg, 1.56 mmol, 6.00 eq.) was then added dropwise; the reaction mixture was heated to 70 °C and stirred, in the darkness, for 13 h. The disappearance of starting materials (Rfs 0.65 and 0.42 respec., (2/1) hexane/DCM) was monitored by TLC. The solvent was evaporated, the residue was dissolved in DCM, washed with water and brine and dried over anhydrous MgSO4. After evaporation of the solvent, the crude title compound (261 mg) was column chromatographed on silica gel, using as eluent (5/4) DCM/hexane (Rf 0.46), yielding a mixture of product and impurities with similar Rfs (113 mg); further purification using as eluent (3/2) hexane/DCM (Rf 0.14) afforded the pure product (yellow solid, 86 mg, 104 μmol, yield 40%).
*Yield (%) 40 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p121.pdf
Further information Compound 28: 1,4-bis(2-(4-(2-(4-methylthio)phenyl)ethynyl)phenyl)ethynyl-2,5-bis(octyl-oxy)-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 24: Deprotection of TMS group: 2-(4-(2-(4-(methylthio)phenyl)ethynyl)phenyl)ethynylene

Reaction 27: Halogenation of 1,4-bis(octyloxy)benzene with Iodine: 1,4-diiodo-2,5-bis(octyloxy)benzene

For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p121.pdf
reactionscheme_28 .cdx