ortho-Metalation of Unprotected 3-Bromo and 3-Chlorobenzoic Acids with Hindered Lithium Dialkylamides
| Autor: | Jacques Mortier, Frederic Gohier |
|---|---|
| Rok vydání: | 2003 |
| Předmět: |
chemistry.chemical_classification
Substitution reaction Quenching (fluorescence) Base (chemistry) Lithium bromide Metalation Organic Chemistry chemistry.chemical_element General Medicine Medicinal chemistry chemistry.chemical_compound chemistry Electrophile Organic chemistry Lithium Derivative (chemistry) Chlorobenzoic Acids |
| Zdroj: | ChemInform. 34 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200328095 |
| Popis: | Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at -50 degrees C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2-substituted-3-chloro/bromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting free lithium 2,3- and 3,4-dehydrobenzoates that can be intercepted in situ with the hindered base. |
| Databáze: | OpenAIRE |
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