反応 #59109

反応方程式

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum trichloride

→

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

収率 63.0%

溶媒

dichloroethane

反応条件

後処理

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

実験手順

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).

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