Reaction #2348124

Reaction equation

2-bromo-5-methoxynitrobenzene

4-methoxystyrene

N,N-diisopropylethylamine

→

nitro-stilbene

Yield 79.2%

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

Yield 79.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to room temperature
2. 2
   Otherpartitioned between ethyl acetate and water
3. 3
   OtherThe organic layer was separated
4. 4
   Washwashed with water, brine
5. 5
   Dryingdried over magnesium sulfate
6. 6
   ConcentrationConcentration under reduced pressure
7. 7
   Othergave the crude product which
8. 8
   Otherwas purified by column chromatography

Procedure

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%).

Source