Reaktion #9437

Reaktionsgleichung

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

4-(methansulfonyl)phenylboronic acid

KF

ammonium chloride

→

title compound

{4-[3,3-Bis-(4′-methanesulfonyl-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: ethyl acetate:methanol (9:1))

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 (208 mg, 0.38 mmol, example 1, step A–B), 4-(methansulfonyl)phenylboronic acid (280 mg, 1.4 mmol), KF (77 mg, 1.33 mmol), Pd2(dba)3 (21 mg, 23 mmol) and Pd(P(t-BU)3)2 (23 mg, 46 mmol). THF (5 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: ethyl acetate:methanol (9:1)) to give the title compound in 95 mg (36%) yield.

Quelle