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29th August 2013 @ 10:46

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Reaction information

*#Reaction file
reactionscheme_27 .cdx
*Reaction file type CDX
*Procedure Repeating the procedure described by Shirai, in a 250 mL rbf a solution of 1,4-bis(Octyloxy)benzene (2.04 g, 6.10 mmol), Hg(OAc)2 (4.84 g, 15.19 mmol, 2.49 eq.) and I2 (3.85 g, 15.17 mmol, 2.49 eq.) in DCM (60 mL) was stirred at r.t. for 19 h. The reaction mixture was filtered through Celite 521 with DCM and the organic phase was washed with Na2S2O3 (aqueous, 10% w/v), to the complete disappearance of the pink colour, then with NaHCO(saturated), water and brine, and dried over anhydrous MgSO4. Evaporation of the solvent and recrystallization from EtOH afforded the pure product (3.15 g, 5.37 mmol, yield 88%).
*Yield (%) 88 %
*Type of Yield Isolated pure product

PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p120-121.pdf

Shirai, Y.; Zhao, Y. M.; Cheng, L.; Tour, J. M. OrgLett2004, 6, 13, 2129-2132

Further information Compound 27: 1,4-diiodo-2,5-bis(octyloxy)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 26: Nucleophilic substitition of hydroquinone to octylbromide: 1,4-bis(octyloxy)benzene
For step in multistep reaction - link to following reaction step Reaction 28: Bidirectional Sonogashira Coupling: 1,4-bis(2-(4-(2-(4-methylthio)phenyl)ethynyl)phenyl)ethynyl-2,5-bis(octyl-oxy)-benzene
Attached Files
PhD Thesis - 16Sep2010_final p120-121.pdf
reactionscheme_27 .cdx