Reaktion #468998

Reaktionsgleichung

aluminum chloride

3-carbomethoxypropionyl chloride

4-bromobiphenyl

→

4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester

Ausbeute 77.2%

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITAfter 1 day
2. 2
   Temperaturthe reaction was cooled to 5° C.
3. 3
   Sonstigequenched by the dropwise addition of water (50 mL)
4. 4
   SonstigeThe layers were separated
5. 5
   Waschenthe organic layer washed with water and brine
6. 6
   Trocknendried (MgSO4), and rotary evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved (CH2Cl2)
8. 8
   Sonstigepurified by column chromatography on silica gel
9. 9
   Wascheneluting with dichloromethane

Vorschrift

To a stirred suspension of anhydrous aluminum chloride (3.45 g, 0.026 mol) in dichloromethane (20 mL) at 5° C. was added dropwise a solution of 4-bromobiphenyl (2.3 g, 0.010 mol) in dichloromethane (11 mL) followed by the dropwise addition of 3-carbomethoxypropionyl chloride (1.35 mL, 0.011 mol) in dichloromethane (15 mL), and the mixture stirred. After 2 hours at 5° C., the mixture was allowed to warm to room temperature. After 1 day, the reaction was cooled to 5° C. and quenched by the dropwise addition of water (50 mL). The layers were separated, and the organic layer washed with water and brine, dried (MgSO4), and rotary evaporated. The residue was dissolved (CH2Cl2) and purified by column chromatography on silica gel, eluting with dichloromethane to give 2.68 g of 4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 115.0-116.5° C.

Quelle