1-(4-METHOXYPHENYL)-2-(4-NITROPHENYL)-ACETYLENE synthesis
- Product Name:1-(4-METHOXYPHENYL)-2-(4-NITROPHENYL)-ACETYLENE
- CAS Number:39082-40-1
- Molecular formula:C15H11NO3
- Molecular Weight:253.25
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Yield: 87%
Reaction Conditions:
Stage #1:para-iodoanisole;trimethylsilylacetylene with potassium carbonate in methanol;acetonitrile at 40; for 2 h;Sonogashira Cross-Coupling;
Stage #2:p-nitrobenzene iodide in methanol;acetonitrile at 40; for 2 h;chemoselective reaction;Sonogashira Cross-Coupling;
Steps:
2.2 General procedure for synthesis of diarylacetylenes
General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40°C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.
References:
Mandali, Pavan Kumar;Chand, Dillip Kumar [Catalysis Communications,2014,vol. 47,p. 40 - 44]
