تفاعل #2348124

معادلة التفاعل

2-bromo-5-methoxynitrobenzene

4-methoxystyrene

N,N-diisopropylethylamine

→

nitro-stilbene

المردود 79.2%

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

المردود 79.2%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was cooled to room temperature
2. 2
   أخرىpartitioned between ethyl acetate and water
3. 3
   أخرىThe organic layer was separated
4. 4
   غسيلwashed with water, brine
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   تركيزConcentration under reduced pressure
7. 7
   أخرىgave the crude product which
8. 8
   أخرىwas purified by column chromatography

الإجراء التجريبي

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%).

المصدر