| Автор | Ladd, David L. |
| Автор | Gaitanopoulos, Dimitri |
| Автор | Weinstock, Joseph |
| Дата выпуска | 1985 |
| dc.description | AbstractIn a previous paper<sup>1</sup> we reported the synthesis of 3-fluoro-veratrole (1) from fi-fluoroanisole via low temperature lithiation followed by reaction with trimethyl borate and peroxide oxidation followed by methylation (Scheme I). In subsequent larger scale preparations decreased yields of 1 have been observed. We have identified<sup>2</sup> 2 as the major by-product, no doubt being formed via a benzyne pathway<sup>3</sup> which becomes more significant as reaction times become longer during 1 arger scale preparations. Therefore we required a method suitable for larger scale preparations of 1. In addition, our previous work used chloromethylation in order to introduce a carbon in to the 4-position of 1. In order to avoid this potentially hazardous reaction, we desired a method not involving chloromethylation to obtain 2-fluoro-3,4-dimethoxybenz-aldehyde (3). The methods that we have developed are shown in Scheme II. |
| Формат | application.pdf |
| Издатель | Taylor & Francis Group |
| Копирайт | Copyright Taylor and Francis Group, LLC |
| Название | A New Synthesis of 3-Fluoroveratrole and 2-Fluoro-3, 4-Dimethoxybenzaldehyde |
| Тип | research-article |
| DOI | 10.1080/00397918508063780 |
| Electronic ISSN | 1532-2432 |
| Print ISSN | 0039-7911 |
| Журнал | Synthetic Communications |
| Том | 15 |
| Первая страница | 61 |
| Последняя страница | 69 |
| Аффилиация | Ladd, David L.; Department of Medicinal Chemistry Research, Development Division Smith Kline & French Laboratories |
| Аффилиация | Gaitanopoulos, Dimitri; Department of Medicinal Chemistry Research, Development Division Smith Kline & French Laboratories |
| Аффилиация | Weinstock, Joseph; Department of Medicinal Chemistry Research, Development Division Smith Kline & French Laboratories |
| Выпуск | 1 |
| Библиографическая ссылка | David Ladd, L. and Weinstock, Joseph. 1981. J. Org. Chem., 46: 203 |
| Библиографическая ссылка | Identified as the trimethoxy derivative (2a, mp: 91–92. 5°C, acetone) which was prepared by refluxing 2 with excess dimethyl sulfate and K<sub>2</sub>CO<sub>3</sub> in acetone; 360 MHz lH NMR (CDCl<sub>3</sub>) showed three OCH<sub>3</sub>'s at 3. 67, 3. 77 and 3. 92; CI mass spectrum m/e 263 (M+H). Anal. Calcd for C<sub>l5</sub>H<sub>l5</sub>FO<sub>3</sub>: C, 68.69; H, 5. 76. Found: C, 68. 65; H, 5. 77 |
| Библиографическая ссылка | Wakefield, B. J. 1974. “The Chemistry of Organolithium Compounds”, 172Oxford: Pergamon Press. |
| Библиографическая ссылка | Ogino, T. and Mochizuki, K. 1979. Chem. Lett., 443 |
| Библиографическая ссылка | Godfrey, I. M., Sargent, M. V. and Elix, J. A. 1974. J. C. S. Perkin I, 1353 |
| Библиографическая ссылка | Suzuki, Y. and Takahashi, H. 1983. Chem. Pharm. Bull., 31: 1751 |
| Библиографическая ссылка | GC/MS showed two components with m/e 353 [(M+H)<sub>+</sub> corresponding to ll] and two components with m/e 492 (M<sup>+</sup> corresponding to 12). GC/IR showed two components with aromatic aldehyde carbonyl absorption at 1706 cm<sup>−l</sup> corresponding to 11 and nine components lacking carbonyl absorptions and differing only in the 1142–1008 cm<sup>−1</sup> region (aromatic C-F and ring substitutions) consistent with the isomers of 12 |
| Библиографическая ссылка | Ogata, Y., Kowasaki, A. and Sugiura, F. 1968. Tetrahedron, 24: 5001 |
| Библиографическая ссылка | U. S. Patent, 4, 124, 643. 1978. (To UOP, Inc., Des Plains, Ill.) |
| Библиографическая ссылка | Kirk, K. L. 1976. J. Org. Chem., 41: 2373 |
