Potassium Carbonate → 3,4-Dichlorobiphenyl

Temperatur

120 °C

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.

1. customnitrogen bubbled into it for 20 minutes
2. additionPalladium acetate was added (0.99 g, 4.425 mmol)
3. temperatureCooled to room temperature
4. additiondiluted with water and dichloromethane
5. filtrationThe mixture was filtered through Celite
6. washthe Celite was washed with water and dichloromethane
7. customThe layers were separated
8. extractionthe aqueous layer extracted with dichloromethane
9. dry with materialThe organic layers were dried over magnesium sulfate
10. filtrationfiltered
11. customevaporated
12. customto yield a brown oil
13. customThe crude material was purified by column chromatography
14. washeluting with hexanes
15. additionThe cleanest fractions containing product
16. customwere collected

ORD-Eintrag

ord-71e60726b9564c6eafbbcc638fd40fe9

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08652652B2