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Reaction id: 0501011088_12, verified by Personal Chemistry ©
Mo(CO)6
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2-Bromobenzamide
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dppf
DIEA
DMAP
Pd(OAc)2
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1,4-Dioxane
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23p
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Yield: 70% Time: 1800s Temperature: 150 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 13939-06-5 |
264.000 |
1.000 |
0.500 |
132.000 µl |
| 4001-73-4 |
200.040 |
1.000 |
1.000 |
200.040 µl |
| DMAP |
122.171 |
1.000 |
2.000 |
244.342 µl |
| dppf |
554.393 |
1.104 |
0.050 |
25.108 µl |
| Pd(OAc)2 |
224.488 |
1.000 |
0.050 |
11.224 µl |
| DIEA |
129.247 |
0.755 |
2.000 |
342.376 µl |
| 1,4-Dioxane |
88.106 |
1.034 |
11.736 |
1000.000 µl |
| Product 1 |
147.133 |
1.000 |
0.000 |
0.000 µl |
Keywords
Carboxylation, Catalysis, Catalyzed, Cyclisation, Heterocyclisation, Metal, Ring closure, Ring formation
Comments
Synthesis: This reaction type was also attempted using DMF as a carbon monoxide source. During these conditons, however, the dominating reaction was debromination of the starting material and the best yield obtained for the model reaction was 45% (compared to 88% using this Mo(CO)6 based method). Using the method described here, both electron rich and electron poor substrates gave the desired products from both primary and secondary benzyl alcohols. With a nitro substituent on the phenyl ring, reduction of this group took place instead of the carboxylation and ring formation. The reaction vial was flushed with nitrogen before it was capped and heated.
Work-up and purification: After the reaction, the mixture was diluted with ethyl acetate and washed with water and brine. The solution was then dried over K2CO3, and the solvent removed. The product was purified by column chromatography.
Characterisation: Analytical data were in correspondance with published material.
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Wu, X.; Mahalingam, A. K.; Wan, Y.; Alterman, M. Tet. Lett. 2004, 24, 4635-4638
Analysis
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