反応 #2348124

反応方程式

2-bromo-5-methoxynitrobenzene

4-methoxystyrene

N,N-diisopropylethylamine

→

nitro-stilbene

収率 79.2%

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

収率 79.2%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度The reaction mixture was cooled to room temperature
2. 2
   その他partitioned between ethyl acetate and water
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with water, brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   濃縮Concentration under reduced pressure
7. 7
   その他gave the crude product which
8. 8
   その他was purified by column chromatography

実験手順

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%).

出典