Reacción #9637

Ecuación de reacción

bromobenzene

AlCl3

HCl

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

→

cis-2-(4-bromobenzoyl)cyclopropanecarboxylic acid

Rendimiento 74.6%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe solution was stirred for few minutes
3. 3
   Otrothe layers were separated
4. 4
   ExtracciónThe aqueous layer was extracted with DCM
5. 5
   Lavadothe combined organic phases were washed with water, brine
6. 6
   Secadodried over Na2SO4
7. 7
   Concentraciónconcentrated

Procedimiento

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).

Fuente