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28th August 2013 @ 10:06

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Reaction information

*#Reaction file
reactionscheme_19 .cdx
*Reaction file type CDX
*Procedure In a 500 mL rbf a solution of 4-(2-(Trimethylsilyl)ethynyl)benzonitrile (1.49 g, 7.47 mmol) in MeOH (200 mL) was stirred for 3 h in presence of K2CO3 (10.32 g, 74.67 mmol, 10.00 eq.), the disappearance of starting material was monitored by TLC. Water was poured in the flask until all the carbonate was dissolved, and the solution was extracted with DCM three times; the combined organic phases were washed with brine, and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude product (1.02 g) that was column chromatographed on silica gel, using DCM as eluent (Rf 0.57), to obtain the pure title compound (0.74 g, 5.82 mmol, yield 78%).
*Yield (%) 78 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p116.pdf
Further information Compound 19: 4-ethynylbenzonitrile

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 18: Sonogashira Coupling: 4-(2-(Trimethylsilyl)ethynyl)benzonitrile
For step in multistep reaction - link to following reaction step Reaction 20: Bidirectional Sonogashira Coupling: 1,4-didodecyl-2,5-bis-(2-(4-cyanobenzil)ethynyl)benzene
Attached Files
PhD Thesis - 16Sep2010_final p116.pdf
reactionscheme_19 .cdx