1-Phenyl-2-(2-chlorophenyl)ethyne synthesis
- Product Name:1-Phenyl-2-(2-chlorophenyl)ethyne
- CAS Number:10271-57-5
- Molecular formula:C14H9Cl
- Molecular Weight:212.67
Yield:10271-57-5 100%
Reaction Conditions:
with bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;triethylamine at 30; for 24 h;Inert atmosphere;Sealed tube;Sonogashira Cross-Coupling;
Steps:
General Procedure A: Optimized conditions
General procedure: For example, synthesis of 1,2-diphenylethyne, 3a. To an oven-dried 5 mL microwave vessel was added Pd(PPh3)2Cl2 (3.5 mg, 0.005 mmol, 2 mol %) and CuI (1.9 mg, 0.01 mmol, 4 mol %). The vessel was then capped and purged with N2 before addition of Cyrene (0.5 mL, 0.5 M), Et3N (38 μL, 0.275 mmol, 1.1 equiv), iodobenzene (27.9 μL, 0.25 mmol, 1 equiv), and phenylacetylene (28.8 μL, 0.263 mmol, 1.05 equiv). The reaction mixture was heated to 30 °C and maintained at this temperature with stirring for 1 h before the vessel was vented, and decapped. The solution was then diluted with EtOAc (10 mL), and washed with water (2× 20 mL) and brine (2 × 20 mL). The organics were then passed through a hydrophobic frit and concentrated under reduced pressure to give a yellow oil, which was purified by flash chromatography (silica gel, 0-5% Et2O in petroleum ether) to afford the title compound as a white solid (44.5 mg, quant.).
References:
Wilson, Kirsty L.;Kennedy, Alan R.;Murray, Jane;Greatrex, Ben;Jamieson, Craig;Watson, Allan J. B. [Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2005 - 2011] Location in patent:supporting information
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