تفاعل #59109

معادلة التفاعل

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum trichloride

→

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

المردود 63.0%

المذيبات

dichloroethane

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر