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23rd August 2013 @ 08:44

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Reaction information

*#Reaction file
reactionscheme_6 .cdx
*Reaction file type CDX
*Procedure To a stirred solution of 1,4-Didodecylbenzene (11.18 g, 26.95 mmol) in DCM (68 mL), in a 500 mL rbf, were added I2 (27.36 g, 107.8 mmol, 4.00 eq.), H5IO6(18.43 g, 80.85 mmol, 3.00 eq.), CH3COOH (80 mL) and concentrated H2SO4(11 mL); the mixture was heated to 95 ºC and stirred in the darkness for 20 h, and the disappearance of starting material was monitored by TLC, using as eluent (20/1) hexane/DCM . The reaction mixture was then poured in water and extracted twice with Et2O; the combined organic phases were washed with Na2S2O3 (aqueous, 10% w/v) until there had been complete disappearance of the pink colour, and three times with water, and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude title compound (16.695 g); the product, as recrystallized from (6/1) EtOH/ethyl acetate (tiny white needles, 13.61 g, 20.42 mmol, yield 76%).
*Yield (%) 76 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p12.pdf
 
PhD Thesis - 16Sep2010_final p107-108.pdf
Further information Compound 6: 1,4-Didodecyl-2,5-diiodobenzene

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 5: Nickel-catalysed Alkylation of dichlorobenzene with dodecylmagnesium bromide: 1,4-didodecylbenzene
For step in multistep reaction - link to following reaction step

Reaction 7: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(trimethylsilyl)ethynyl)benzene

Reaction 20: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis-(2-(4-cyanobenzil)ethynyl)benzene

Reaction 25: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis(2-(4-(2-(4-methylthio)phenyl)ethynyl)phenyl)-ethynyl-benzene

Attached Files
PhD Thesis - 16Sep2010_final p107-108.pdf
reactionscheme_6 .cdx