Reaktion #488331

Reaktionsgleichung

N-methoxy-N-methyl-2-phenyl-acetamide

1-phenyl-2-m-tolylethanone

Intermediate 4

1-phenyl-2-m-tolylethanone

4-bromobiphenyl

n-BuLi

→

1-(biphenyl-4-yl)-2-phenylethanone

Ausbeute 24.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at −78° C. for 2 h
2. 2
   SonstigeThe reaction was quenched with saturated NH4Cl aqueous solution
3. 3
   Extraktionextracted with EtOAc
4. 4
   TrocknenThe organic layer was dried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigepurified by column chromatography (PE:EtOAc=20:1)

Vorschrift

To a solution of 4-bromobiphenyl (683 mg, 2.9 mmol) in anhydrous THF (5 mL) was added n-BuLi (1.2 mL, 2.9 mmol) dropwise at −78° C. After being stirred at the temperature for 0.5 h, a solution of N-methoxy-N-methyl-2-phenyl-acetamide (prepared following step 1 of Intermediate 4) (500 mg, 2.8 mmol) in anhydrous THF (5 mL) was added via a syringe, and the mixture was stirred at −78° C. for 2 h. The reaction was quenched with saturated NH4Cl aqueous solution, and extracted with EtOAc. The organic layer was dried over Na2SO4, concentrated in vacuo, and purified by column chromatography (PE:EtOAc=20:1) to give 1-(biphenyl-4-yl)-2-phenylethanone (180 mg, yield 24%).

Quelle