Реакция #2006424

Уравнение реакции

4-bromocinnamic acid

ammonium chloride

→

beige solid

Выход 73.0%

3-(4-Bromophenyl)-propanoic Acid

Выход 73.0%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Температураat reflux for 12 hours
2. 2
   Экстракцияthe aqueous layer was extracted with ethyl acetate 3 times
3. 3
   ПромывкаCombined organic layers were washed with water and brine
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under vacuo
7. 7
   ДругоеThe resulting solid was purified by flash chromatography
8. 8
   Промывкаeluting with 5% methanol

Методика

Under nitrogen atmosphere in a 250 mL round bottomed flask containing 4-bromocinnamic acid (5.0 g, 22 mmoles) in 45 mL of N,N-dimethylformamide (0.5 M) was added benzenesulfonylhydrazide (7.6 g, 44 mmoles). The mixture was stirred at reflux for 12 hours. The solution was cooled at room temperature, aqueous saturated ammonium chloride was added and the aqueous layer was extracted with ethyl acetate 3 times. Combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuo. The resulting solid was purified by flash chromatography eluting with 5% methanol:95% dichloromethane to afford 3.66 g (73%) of beige solid.

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