Реакция #328673

Уравнение реакции

1-Bromo-3,4-dichlorobenzene

phenylboronic acid

triphenylphosphine

potassium carbonate

→

clean product

Выход 30.4%

4-Phenyl-1,2-dichlorobenzene

Выход 30.4%

Растворители

water

Условия реакции

Обработка

1. 1
   Другоеnitrogen bubbled into it for 20 minutes
2. 2
   workup.ADDITIONPalladium acetate was added (0.99 g, 4.425 mmol)
3. 3
   ТемператураCooled to room temperature
4. 4
   workup.ADDITIONdiluted with water and dichloromethane
5. 5
   ФильтрацияThe mixture was filtered through Celite
6. 6
   Промывкаthe Celite was washed with water and dichloromethane
7. 7
   ДругоеThe layers were separated
8. 8
   Экстракцияthe aqueous layer extracted with dichloromethane
9. 9
   СушкаThe organic layers were dried over magnesium sulfate
10. 10
    Фильтрацияfiltered
11. 11
    Другоеevaporated
12. 12
    Другоеto yield a brown oil
13. 13
    ДругоеThe crude material was purified by column chromatography
14. 14
    Промывкаeluting with hexanes
15. 15
    workup.ADDITIONThe cleanest fractions containing product
16. 16
    Другоеwere collected

Методика

A mixture was prepared of 1-Bromo-3,4-dichlorobenzene (20.0 g, 88.5 mmol), phenylboronic acid (13.5 g, 110.6 mmol), triphenylphosphine (2.32 g, 8.85 mmol), potassium carbonate (30.58 g, 221.25 mmol), 150 mL xylenes, and 150 mL water. The mixture was stirred and nitrogen bubbled into it for 20 minutes. Palladium acetate was added (0.99 g, 4.425 mmol) and the mixture was heated at 120° C. under nitrogen overnight. Cooled to room temperature and diluted with water and dichloromethane. The mixture was filtered through Celite and the Celite was washed with water and dichloromethane. The layers were separated and the aqueous layer extracted with dichloromethane. The organic layers were dried over magnesium sulfate, filtered, and evaporated to yield a brown oil. The crude material was purified by column chromatography eluting with hexanes. The cleanest fractions containing product were collected. Obtained 6 g (30%) of clean product.

Источник