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22nd August 2013 @ 13:36

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Reaction information

*#Reaction file  
*Reaction file type CDX

General procedure B with N-(2-hex-1-ynylphenyl)-4-methyl-benzenesulfonamide (1.48 g, 5.0 mmol) and (Bromoethynyl)benzene (905 mg, 5.0 mmol).  Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as an orange oil (832 mg, 42%).



General procedure B:

A solution of the appropriate bromide (1 eq.) and N,N‑dimethylethylenediamine (0.2 eq.) in dry toluene (20 mL) was added to the appropriate sulfonamide (1 eq.), K3PO4 (2 eq.) and CuI (0.05 eq.) in toluene (10.0 mL).  The reaction mixture was heated to reflux for 16 h.  The reaction mixture was filtered through a plug of silica using ether to elute and the solvent removed in vacuo to give the crude product, which was purified as described.

*Yield (%)  42
*Type of Yield Isolated product yield
AH Thesis_2011_pp93.pdf
AH Thesis_2011_pp176-223.pdf
Further information  Compound 117f: 4-Methyl-N-(phenylethynyl)-N-(4-(trimethylsilyl)but-3-yn-1-yl)benzenesulfonamide

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
AH Thesis_2011_pp93.pdf
AH Thesis_2011_pp176-223.pdf