تفاعل #9637

معادلة التفاعل

bromobenzene

AlCl3

HCl

3-oxabicyclo[3.1.0]hexane-2,4-dione

→

cis-2-(4-bromobenzoyl)cyclopropanecarboxylic acid

المردود 74.6%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe solution was stirred for few minutes
3. 3
   أخرىthe layers were separated
4. 4
   استخلاصThe aqueous layer was extracted with DCM
5. 5
   غسيلthe combined organic phases were washed with water, brine
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated

الإجراء التجريبي

To a cold (0° C.) stirred solution of bromobenzene (9.09 g, 57.89 mmol) and AlCl3 (18.36 g, 137.84 mmol) in dry DCM (150 mL) was added 3-oxabicyclo[3.1.0]hexane-2,4-dione (5.40 g, 48.24 mmol). The reaction mixture was stirred at rt for 3 days. The dark-red solution was then poured into ice-cold water (120 mL), and conc. HCl (10 mL) was added. The solution was stirred for few minutes, and the layers were separated. The aqueous layer was extracted with DCM and the combined organic phases were washed with water, brine, dried over Na2SO4 and concentrated to give cis-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (9.69 g, 65%). LC-MS ret. time 2.50; m/z 270 (MH+); 1H NMR (400 MHz, CD2Cl2) δ 1.54 (m, 1H), 1.85 (m, 1H), 2.37 (m, 1H), 2.88 (m, 1H), 7.65 (m, 2H), 7.90 (m, 2H).

المصدر