反应 #9615

反应方程式

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum

→

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

收率 63.0%

溶剂

dichloroethane

反应条件

后处理

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

实验过程

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).

来源