反応 #2006424

反応方程式

4-bromocinnamic acid

ammonium chloride

→

beige solid

収率 73.0%

3-(4-Bromophenyl)-propanoic Acid

収率 73.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度at reflux for 12 hours
2. 2
   抽出the aqueous layer was extracted with ethyl acetate 3 times
3. 3
   洗浄Combined organic layers were washed with water and brine
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under vacuo
7. 7
   その他The resulting solid was purified by flash chromatography
8. 8
   洗浄eluting with 5% methanol

実験手順

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.

出典