Reacción #2006424

Ecuación de reacción

4-bromocinnamic acid

ammonium chloride

→

beige solid

Rendimiento 73.0%

3-(4-Bromophenyl)-propanoic Acid

Rendimiento 73.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 12 hours
2. 2
   Extracciónthe aqueous layer was extracted with ethyl acetate 3 times
3. 3
   LavadoCombined organic layers were washed with water and brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated under vacuo
7. 7
   OtroThe resulting solid was purified by flash chromatography
8. 8
   Lavadoeluting with 5% methanol

Procedimiento

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.

Fuente