Реакция #2320124

Уравнение реакции

6-bromo-3-methylpyridine

phenylboronic acid

triphenylphosphine

K2CO3

→

3-methyl-6-phenylpyridine

Выход 84.1%

Растворители

dimethoxyethane

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураat reflux for 20 hours
3. 3
   ЭкстракцияThe aqueous phase was extracted twice with 200 mL of ethyl acetate
4. 4
   ЭкстракцияThe combined organic extractions
5. 5
   Экстракцияwere then extracted with brine
6. 6
   Сушкаdried over magnesium sulfate
7. 7
   ДругоеThe filtrate was evaporated in vacuo
8. 8
   workup.DISTILLATIONthe resultant oil purified by Kugelehor distillation (190° C. @ 500 microns)

Методика

To a 2 L flask, 45.0 g (262 mmol) of 6-bromo-3-methylpyridine, 38.3 g (314 mmol) of phenylboronic acid, 1.47 g (6.54 mmol) of palladium acetate, 6.86 g (26.2 mmol) of triphenylphosphine and 353 mL of 2M K2CO3 were added to 405 mL of dimethoxyethane. The mixture was heated at reflux for 20 hours and cooled to room temperature. The aqueous phase was extracted twice with 200 mL of ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The filtrate was evaporated in vacuo and the resultant oil purified by Kugelehor distillation (190° C. @ 500 microns) to give 37.2 g (84.1% yield) of 3-methyl-6-phenylpyridine as white solids.

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