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Reaction id: 0503011001_02, verified by Personal Chemistry ©
2-Fluorobenzonitrile
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Phenol
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K2CO3
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CH3CN
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Product 1
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Yield: 99% Time: 1800s Temperature: 210 °C
Chemicals
| Name |
MW [g/mol] |
Density [g/ml] |
Amount [mmol] |
Mass/Volume |
| 394-47-8 |
121.114 |
1.110 |
1.000 |
109.112 µl |
| 108-95-2 |
94.113 |
1.000 |
1.000 |
94.113 mg |
| K2CO3 |
138.204 |
1.000 |
1.200 |
165.845 mg |
| CH3CN |
41.053 |
1.000 |
73.076 |
3000.000 µl |
| Product 1 |
195.221 |
1.000 |
1.000 |
195.221 mg |
Keywords
Nucleophilic aromatic substitution, O-Arylation, SNAr
Comments
Synthesis: During optimisation, the reaction type was also performed in DMSO and NMP, but acetonitrile was chosen as solvent, since it is easier to remove. In order to obtain complete conversion in acetonitrile, the highest possible temperature and prolonged reaction time is required.
Work-up: The solids were filtered off and washed with 6 mL acetonitrile. The solution was concentrated on rotavapor.
Purification: The crude material was purified by chromatography on Horizon HPFC System using a prepacked silica column cartridge, starting with heptane-ethyl acetate 3:1 and increasing the polarity of the eluent system to 2:1.
Characterisation: By 1H NMR
Instrument Settings
Absorption level: Normal
Pre-stirring time: 0s
References
Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith III, W. J. J. Org. Chem. 1998, 63, 6338-6343
Ioannidis, P.; Lundin, R. 229th ACS National Meeting & Exposition March 13-17th, 2005, San Diego, CA
Analysis
| Method |
Purity |
Files |
| LC-MS |
99 |
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