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Reaction id: 0501011073_11, verified by Personal Chemistry ©
Zinc cyanide
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5-Iodoindole
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PS-PPh3
Pd(OAc)2
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DMF
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p11
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Yield: 96% Time: 3000s Temperature: 140 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 557-21-1 |
117.406 |
1.000 |
1.000 |
117.406 µl |
| 16066-91-4 |
243.047 |
1.000 |
1.000 |
243.047 mg |
| Pd(OAc)2 |
224.488 |
1.000 |
0.067 |
15.000 mg |
| PS-PPh3 (3.0 mmol/g, PS) |
261.284 |
1.000 |
0.150 |
50.000 mg |
| DMF |
73.095 |
0.940 |
38.580 |
3000.000 µl |
| Product 1 |
142.161 |
1.000 |
0.000 |
0.000 mg |
Keywords
Aromatic, Catalysis, Catalyzed, Metal, Nucleophilic, Nucleophilic aromatic substitution, Solid supported, Substitution
Comments
Synthesis: The solid supported PPh3, palladium acetate and DMF were first mixed, purged with nitrogen and left stirring at room temperature for 2 hours. The vial was then opened, the zinc cyanide and aryl halide were added and the resulting mixture purged once more before heating.
Work-up and purification: After the reaction, the mixture was filtered through a glass frit and the resin was washed with 3*10 ml diethyl ether. The combined organic solutions were washed with 3*5 ml water and 10 ml brine and then dried over MgSO4. Evaporation of the solvent gave the product in >90% purity.
Characterisation: By HPLC and 1H NMR.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Srivastava, R. R.; Collibee, S. E. Tet. Lett. 2004, 48, 8895-8897
Analysis
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