Реакция #2348124

Уравнение реакции

2-bromo-5-methoxynitrobenzene

4-methoxystyrene

N,N-diisopropylethylamine

→

nitro-stilbene

Выход 79.2%

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

Выход 79.2%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture was cooled to room temperature
2. 2
   Другоеpartitioned between ethyl acetate and water
3. 3
   ДругоеThe organic layer was separated
4. 4
   Промывкаwashed with water, brine
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   КонцентрированиеConcentration under reduced pressure
7. 7
   Другоеgave the crude product which
8. 8
   Другоеwas purified by column chromatography

Методика

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%).

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