Reaktion #513489

Reaktionsgleichung

(5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

4-chlorophenyl boronic acid

K2CO3

→

(4″-chloro-4-trifluoromethyl-[1,1′;3′,1″]terphenyl-5′-yl)-acetic acid methyl ester

Lösungsmittel

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   workup.ADDITIONdiluted with EtOAc
3. 3
   Waschenwashed with Na2CO3, dil HCl, brine
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   Sonstigeto give an off white solid
7. 7
   SonstigeThe residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

Vorschrift

A solution of (5-trifluoromethanesulfonyloxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (100 mg, 0.2 mmol), 4-chlorophenyl boronic acid (41 mg, 0.24 mmol), K2CO3 (2 M solution in H2O, 220 μL, 0.4 mmol) in DME (2.0 mL) was heated to 80° C. in the presence of bis(tri-t-Butylphosphine) palladium (0) (cat) for 2 hrs. The mixture was cooled to room temperature filtered, diluted with EtOAc, washed with Na2CO3, dil HCl, brine, dried (MgSO4) and evaporated under reduced pressure to give an off white solid. The residue was purified by flash column chromatography (EtOAc:petroleum ether), 1H NMR (CDCl3) δ 7.71 (s, 4H), 7.65-7.68 (m, 1H), 7.42 (d, 2H), 7.52-7.48 (m, 2H), 7.36 (d, 2H), 3.77 (s, 2H), 3.74 (s, 3H)

Quelle