Reaktion #54024

Reaktionsgleichung

4-bromonitrobenzene

2-methoxyphenyl boronic acid

→

2-methoxy-4′-nitrobiphenyl

Ausbeute 72.4%

Lösungsmittel

ethylene glycol dimethyl ether

sodium carbonate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with argon gas
2. 2
   workup.ADDITION3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere
3. 3
   TemperaturThe reaction mixture was cooled down to room temperature
4. 4
   FiltrationThe mixture was filtered through diatomaceous earth
5. 5
   workup.ADDITIONthe filtrate was diluted with water
6. 6
   Extraktionthe product was extracted three times with EtOAc
7. 7
   Trocknendried over magnesium sulfate (MgSO4)
8. 8
   Sonstigethe solvent was evaporated in vacuo
9. 9
   SonstigeThe residue was purified by flash chromatography

Vorschrift

A mixture of 20.8 g of 4-bromonitrobenzene and 17.2 g of 2-methoxyphenyl boronic acid in 340 mL of ethylene glycol dimethyl ether and 170 mL of 2 M sodium carbonate solution was purged with argon gas and then 3.6 g of Pd(PPh3)2Cl2 was added under argon atmosphere. The reaction mixture was heated in a sealed flask at 120° C. overnight. The reaction mixture was cooled down to room temperature. The mixture was filtered through diatomaceous earth and the filtrate was diluted with water and the product was extracted three times with EtOAc. The organic layers were combined, dried over magnesium sulfate (MgSO4), and the solvent was evaporated in vacuo. The residue was purified by flash chromatography to yield 17.1 g of 2-methoxy-4′-nitrobiphenyl as a solid.

Quelle