Reaktion #64999

Reaktionsgleichung

sodium carbonate

phenylboronic acid

ethanol

1-bromo-4-nitrobenzene

→

desired product

Ausbeute 127.3%

4-nitrobiphenyl

Ausbeute 127.3%

Lösungsmittel

EtOAc

dimethoxy-ethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter a further 10 minutes
2. 2
   Temperaturthe suspension was heated
3. 3
   Temperaturat reflux for 20 minutes
4. 4
   ExtraktionThe aqueous layer was extracted with 200 ml of EtOAc
5. 5
   Waschenthe combined organics were washed twice with 250 ml of water and 100 ml of brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

12.50 g (61.9 mmol) of 1-bromo-4-nitrobenzene were added to 358 mg, (310 μmol, 0.5 mole %) of tetrakis (triphenyl-phosphine) palladium in 200 ml of dimethoxy-ethane. After stirring for 10 minutes, 11.3 g (92.8 mmol) of phenylboronic acid and 100 ml of ethanol were added. After a further 10 minutes, 263 ml, (526 mmol, 8.5 equiv) of 2M aqueous sodium carbonate were added and the suspension was heated at reflux for 20 minutes, then allowed to cool to room temperature. The mixture was taken into 250 ml of EtOAc and 200 ml of H2. The aqueous layer was extracted with 200 ml of EtOAc and the combined organics were washed twice with 250 ml of water and 100 ml of brine, dried over MgSO4, filtered and evaporated to obtain 15.7 g of the desired product as a solid.

Quelle