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23rd August 2013 @ 14:02

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Reaction information

*#Reaction file
reactionscheme_13 .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  (624 mg, 0.94 mmol), 1-bromo-4-iodobenzene (585 mg, 2.07 mmol, 2.20 eq.), PdCl2 (33 mg, 0.19 mmol, 20 mol%), PPh3 (99 mg, 0.38 mmol, 40 mol%) and CuI (36 mg, 0.19 mmol, 20 mol%), with stirring, was evacuated under HV and refilled with Ar before adding distilled benzene (15 mL). TEA (0.79 mL, 571 mg, 5.64 mmol, 6.00 eq.) was then added dropwise and the reaction mixture was heated to 70 ºC and stirred in the darkness for 12 h; the disappearance of starting material (Rf 0.10, hexane) was monitored by TLC. The solvent was evaporated and the residue dissolved in DCM, the solution was washed with water and brine and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude title compound (1.125 g). The pure product (white solid, presence of bright yellow imp.; 191 mg, 0.19 mmol, yield 21%) was obtained by column chromatography on silica gel [first column: eluent (20/1) hexane/DCM (Rf 0.13), then (1/1) hexane/DCM (Rf 0.86); second column (3/1) hexane/DCM (R0.58)]. 
*Yield (%) 21 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p13.pdf
PhD Thesis - 16Sep2010_final p111-112.pdf
Further information Compound 13: 1,4-Didodecyl-2,5-bis(2-(4-(2-(4-bromophenyl)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 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 Reaction 14: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-(2-(trimethylsilyl)ethynyl)phenyl)ethynyl) phenyl)ethynyl)benzene
Attached Files
reactionscheme_13 .cdx
PhD Thesis - 16Sep2010_final p111-112.pdf
PhD Thesis - 16Sep2010_final p13.pdf