Reaktion #9615

Reaktionsgleichung

bromobenzene

3,3-dimethyldihydro-2,5-furandione

aluminum

→

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

Ausbeute 63.0%

Lösungsmittel

dichloroethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

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