반응 #59109

반응 방정식

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum trichloride

→

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

수율 63.0%

용매

dichloroethane

반응 조건

후처리

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

실험 절차

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 trichloride (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).

출처