تفاعل #9639

معادلة التفاعل

Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate

NaOH

→

trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid

المردود 96.0%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىSolvent was removed by rotary evaporation
2. 2
   workup.DISSOLUTIONthe residue was dissolved in water
3. 3
   workup.ADDITIONConcentrated HCl was added
4. 4
   أخرىThe precipitate that formed
5. 5
   ترشيحwas collected by filtration
6. 6
   أخرىdried in a vacuum oven overnight

الإجراء التجريبي

Methyl cis-2-(4-bromobenzoyl)cyclopropanecarboxylate (10.34 g, 36.52 mmol) was dissolved in MeOH (100 mL), and then 15 mL 50% aqueous NaOH solution was added. The reaction mixture was stirred at 40° C. for 3 days. Solvent was removed by rotary evaporation and the residue was dissolved in water. Concentrated HCl was added to adjust the acidity to pH 1. The precipitate that formed was collected by filtration and dried in a vacuum oven overnight to give trans-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.43 g, 95%). LC-MS ret. time 2.51, m/z 270 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.68 (m, 2H), 2.38 (m, 1H), 3.22 (m, 1H), 7.67 (m, 2H), 7.90 (m, 2H).

المصدر