Reacción #9615

Ecuación de reacción

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum

→

4-(4-bromophenyl)-2,2-dimethyl-4-oxobutanoic acid

Rendimiento 63.0%

Disolventes

dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   TemperaturaThe mixture was again chilled in an ice/water bath
3. 3
   Otroquenched with 1 M aqueous hydrochloric acid
4. 4
   workup.ADDITIONWater (70 mL) was added
5. 5
   Otrothe layers were separated
6. 6
   ExtracciónThe aqueous layer was extracted with ethyl acetate (3×50 mL)
7. 7
   SecadoThe combined organic layers were dried over anhydrous magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe residue was purified by flash chromatography (Biotage apparatus, 17:83 ethyl acetate/hexane)

Procedimiento

To a chilled solution (ice/water bath) of bromobenzene (7.71 g, 49.1 mmol) and 3,3-dimethyldihydro-2,5-furandione (5.99 g, 46.7 mmol) in dichloroethane (150 mL) was added aluminum trichworide (13.28 g, 99.58 mmol). The ice bath was removed and the reaction mixture was stirred at rt overnight. The mixture was again chilled in an ice/water bath, and then quenched with 1 M aqueous hydrochloric acid. Water (70 mL) was added and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage apparatus, 17:83 ethyl acetate/hexane) to give 4-(4-bromophenyl)-2,2-dimethyl-4-oxobutanoic acid as a white solid (8.34 g, 63%). LC-MS: ret. time 2.79 min; m/z 284.8 (MH+); 1H NMR (300 MHz, CDCl3) δ 1.36 (s, 6H), 3.27 (s, 2H), 7.60 (d, 2H), 7.81 (d, 2H).

Fuente