반응 #468998

반응 방정식

aluminum chloride

3-carbomethoxypropionyl chloride

4-bromobiphenyl

→

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

수율 77.2%

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.WAITAfter 1 day
2. 2
   온도the reaction was cooled to 5° C.
3. 3
   기타quenched by the dropwise addition of water (50 mL)
4. 4
   기타The layers were separated
5. 5
   세척the organic layer washed with water and brine
6. 6
   건조dried (MgSO4), and rotary evaporated
7. 7
   workup.DISSOLUTIONThe residue was dissolved (CH2Cl2)
8. 8
   기타purified by column chromatography on silica gel
9. 9
   세척eluting with dichloromethane

실험 절차

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.

출처