反应详情

温度

50 °C

14 g (0.13 mol) of bromoethane were slowly added dropwise, while stirring, to 2.4 g (0.1 mol) of magnesium filings in 70 ml of anhydrous tetrahydrofuran at 30°-40° C. and the mixture was then stirred for a further 30 minutes at 50° C. The Grignard solution thus prepared was transferred into a dropping funnel under nitrogen and was added dropwise to a saturated solution of acetylene in 40 ml of anhydrous tetrahydrofuran, the solution having been saturated at 20° C. During the addition further acetylene was passed in continuously, and this was continued for a further 30-45 minutes after the end of the dropwise addition. 10.8 g (0.05 mol) of 3-(4-fluorophenoxy)-benzaldehyde, dissolved in 50 ml of absolute tetrahydrofuran, were added dropwise to the suspension of ethynyl magnesium bromide, thus prepared, at 25°-30° C., and the mixture was then warmed to 40° C. for 4 hours. Thereafter the reaction batch was cooled to 10° C. and poured into 500 ml of ice-water, and the resulting precipitate was dissolved by adding concentrated hydrochloric acid. The mixture was then extracted twice with 150 ml of ether at a time, the ether phases were dried over sodium sulfate and the ether was then distilled off in vacuo. 7.3 g (61% of theory) of 3-(4-fluorophenoxy)-α-ethynyl-benzyl alcohol were obtained as a yellow oil of boiling point 160°-180° C./3 mm Hg. ##STR27##

1. customThe Grignard solution thus prepared
2. customwas transferred into a dropping funnel under nitrogen
3. customhaving been saturated at 20° C
4. waitthis was continued for a further 30-45 minutes
5. additionafter the end of the dropwise addition
6. customthus prepared, at 25°-30° C.
7. temperaturethe mixture was then warmed to 40° C. for 4 hours
8. temperatureThereafter the reaction batch was cooled to 10° C.
9. dissolutionthe resulting precipitate was dissolved
10. extractionThe mixture was then extracted twice with 150 ml of ether at a time
11. dry with materialthe ether phases were dried over sodium sulfate
12. distillationthe ether was then distilled off in vacuo