Reaktion #2006424

Reaktionsgleichung

4-bromocinnamic acid

ammonium chloride

→

beige solid

Ausbeute 73.0%

3-(4-Bromophenyl)-propanoic Acid

Ausbeute 73.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 12 hours
2. 2
   Extraktionthe aqueous layer was extracted with ethyl acetate 3 times
3. 3
   WaschenCombined organic layers were washed with water and brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuo
7. 7
   SonstigeThe resulting solid was purified by flash chromatography
8. 8
   Wascheneluting with 5% methanol

Vorschrift

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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