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28th August 2013 @ 09:23

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Reaction information

*#Reaction file
reactionscheme_18.cdx
*Reaction file type CDX
*Procedure A 100 mL Schlenk flask containing 4-bromobenzonitrile (1.456 g, 8.00 mmol), PdCl2 (71 mg, 0.40 mmol, 5 mol%), PPh3 (210 mg, 0.80 mmol, 10 mol%) and CuI (76 mg, 0.40 mmol, 5 mol%) was evacuated and refilled with argon before adding distilled THF (60 mL), TEA (3.34 mL, 2.428 g, 24.00 mmol, 3.00 eq.) and TMSA (1.70 mL, 1.178 g, 12.00 mmol, 1.50 eq.) dropwise. The reaction mixture was stirred at r.t. for 3 h and the disappearance of starting material monitored by TLC. The solvent was evaporated and the solid was dissolved in DCM; filtration through silica and evaporation of the solvent afforded the crude title compound (1.820 g) as black oil. The pure product (1.410 g, 7.07 mmol, yield 88%) was obtained by column chromatography on silica gel using (4/1) hexane/DCM as eluent (Rf 0.15).
*Yield (%) 88 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p115.pdf
Further information Compound 18: 4-(2-(trimethylsilyl)ethynyl)benzonitrile

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  
For step in multistep reaction - link to following reaction step Reaction 19: Deprotection of 4-(2-(trimethylsilyl)ethynyl)benzonitrile: 4-ethynylbenzonitrile
Attached Files
PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p115.pdf
reactionscheme_18.cdx