Reaktion #9436

Reaktionsgleichung

{4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid

phenylboronic acid

KF

ammonium chloride

→

title compound

[4-(3,3-Bis-biphenyl-4-yl-allylsulfanyl)-2-methyl-phenoxy]-acetic acid

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn an evaporated schlenk flask kept under nitrogen atmosphere
2. 2
   workup.WAITfollowed by 4 h at 50° C
3. 3
   Extraktionthe mixture was extracted with dichloromethane (2×20 ml)
4. 4
   SonstigeThe organic phases were dried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by column chromatography (eluent: dichloromethane:THF (8:3))

Vorschrift

In an evaporated schlenk flask kept under nitrogen atmosphere were added {4-[3,3-bis-(4-bromo-phenyl)-allylsulfanyl]-2-methyl-phenoxy}-acetic acid (297 mg, 0.54 mmol), phenylboronic acid (152 mg, 1.2 mmol), KF (104 mg, 1.79 mmol), Pd2(dba)3 (30 mg, 33 mmol) and Pd(P(t-Bu)3)2 (33 mg, 65 mmol). THF (6 ml) was added to the solid mixture keeping the mixture under nitrogen. The reaction mixture was stirred at room temperature for 1 h, followed by 4 h at 50° C. A saturated solution of ammonium chloride (5 ml) was added, and the mixture was extracted with dichloromethane (2×20 ml). The organic phases were dried and evaporated. The residue was purified by column chromatography (eluent: dichloromethane:THF (8:3)) to give the title compound in 155 mg (53%) yield.

Quelle