反应详情

3-methyl-2-chloroquinoline (29.71 g, 167 mmol), phenylboronic acid (24.4 g, 200 mmol), triphenylphosphine (4.388 g, 16.7 mmole) and 2M K2CO3 aqueous soln. (225 mL) were dissolved in the 264 mL of ethylene glycol dimethyl ether. To the stirred solution was added palladium acetate (0.94 g, 4.18 mmole) and the mixture was refluxed under N2 for 20 hours. The reaction mixture was cooled and the water was extracted with methylene chloride three times. The combined organic phase was washed with portions of brine. The organic layer was then dried with anhydrous sodium sulfate, filtered, and evaporated of solvent. The crude material was purified by kegelrohr distillation to give 1 (36.31 g, 98.6%).

1. temperaturethe mixture was refluxed under N2 for 20 hours
2. temperatureThe reaction mixture was cooled
3. extractionthe water was extracted with methylene chloride three times
4. washThe combined organic phase was washed with portions of brine
5. dry with materialThe organic layer was then dried with anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated of solvent
8. distillationThe crude material was purified by kegelrohr distillation