Abstract
In dimethylformamide solution, trifluoroethoxylation and methoxylation of 5-chloro-3-trifluoromethylpyridine (2) yield 5-chloro-3-tris(trifluoroethoxyl)methyl pyridine (2a) and a dimethyl ketal of 3-chloronicotinic acid anhydride (2b) with fluorines as leaving groups, respectively. The corresponding reactions of 2,3-dichloro-5-trifluoromethylpyridine (3) only yield the 2-alkoxy-substituted products 3a and 3b with chloro as the leaving group and the 2-dimethylamino product 3c which was formed by the action of solvent dimethylformamide as a nucleophile. Differences in their reaction behaviour and possible mechanisms are also discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 9-12 |
| Number of pages | 4 |
| Journal | Journal of Fluorine Chemistry |
| Volume | 79 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jul 1996 |
| Externally published | Yes |
Keywords
- Alcoholysis
- Ir spectroscopy
- Mass spectrometry
- Nmr spectroscopy
- Pyridine rings
- Trifluoromethyl groups
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