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29th August 2013 @ 11:13

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Reaction information

*#Reaction file
reactionscheme_29 .cdx
*Reaction file type CDX
*Procedure A 250 mL Schlenk flask containing 4-bromothioanisole (2.03 g, 10.0 mmol), PdCl2 (89 mg, 0.5 mmol, 5 mol%), PPh3 (262 mg, 1.0 mmol,  10 mol%) and CuI (95 mg, 0.5 mmol, 5 mol%), with stirring, was evacuated under high vacuum and refilled with Ar before adding distilled benzene (80 mL). Triethylamine, TEA (4.18 mL, 3.04 g, 30.0 mmol, 3.00 eq.) was then added, followed by phenylacetylene (1.21 mL, 1.12 g, 11.0 mmol, 1.10 eq.) dropwise. The reaction mixture was heated to 70 °C, stirred  for 23 h and then stopped before the disappearance of starting material (4-bromothioanisole Rf 0.32, (6/1) hexane/DCM). The solvent was evaporated, the residue was dissolved in DCM and filtered through Celite521; the solution was then washed with water and brine and dried over MgSO4, to afford, after evaporation of the solvent, a mixture of crude title compound and unreacted starting material (3.118 g). The pure product (white solid, 947 mg, 4.22 mmol, yield 42%) was obtained by column chromatography on silica gel using as eluent (6/1) hexane/DCM (Rf 0.17).
*Yield (%) 42 %
*Type of Yield Isolated pure product
PhD Thesis - 16Sep2010_final p15.pdf
PhD Thesis - 16Sep2010_final p121-122.pdf
Further information Compound 29: Methyl(4-(2-phenylethynyl)phenyl)sulfane

For multistep reactions (or their steps):

Overall reaction? True
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  
Attached Files
PhD Thesis - 16Sep2010_final p15.pdf
reactionscheme_29 .cdx
PhD Thesis - 16Sep2010_final p121-122.pdf