Reaktion #2348124

Reaktionsgleichung

2-bromo-5-methoxynitrobenzene

4-methoxystyrene

N,N-diisopropylethylamine

→

nitro-stilbene

Ausbeute 79.2%

3-Nitro-4-[(E)-2-(4-hydroxyphenyl)-vinyl]phenol

Ausbeute 79.2%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water, brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   EinengenConcentration under reduced pressure
7. 7
   Sonstigegave the crude product which
8. 8
   Sonstigewas purified by column chromatography

Vorschrift

To a stirred solution of 2-bromo-5-methoxynitrobenzene (5 g, 21.6 mmol) in dry acetonitrile (60 mL) were added 4-methoxystyrene (3.04 g, 22.6 mmol), N,N-diisopropylethylamine (8.36 g, 64.6 mmol), biphenyl-2-yl-di-t-butyl phosphine (385 mg, 1.3 mmol) and palladium acetate (290 mg, 1.3 mmol). The resulting mixture was heated at 80° C. overnight under N2. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, and dried over magnesium sulfate. Concentration under reduced pressure gave the crude product which was purified by column chromatography using ethyl acetate in hexane (5%-10%) to give the protected nitro-stilbene (4.4 g, 72%).

Quelle