Reaktion #618282

Reaktionsgleichung

Cyclopropylboronic acid

dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine

sodium carbonate

6-bromo-2,4′-difluoro-3-isopropoxybiphenyl-4-carbaldehyde

→

title compound

Ausbeute 97.7%

6-Cyclopropyl-2,4′-difluoro-3-isopropoxybiphenyl-4-carbaldehyde

Ausbeute 97.7%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtrated through celite
2. 2
   ExtraktionThe filtrate was extracted with ethyl acetate
3. 3
   SonstigeThe organic layer was separated
4. 4
   Waschenwashed with water and brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by a silica gel column chromatography (hexane/ethyl acetate)

Vorschrift

Cyclopropylboronic acid (13.8 g), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (6.58 g), tris(dibenzylideneacetone)dipalladium (0) (7.34 g) and 2M aqueous sodium carbonate solution (120 mL) were added to a solution of 6-bromo-2,4′-difluoro-3-isopropoxybiphenyl-4-carbaldehyde (28.5 g) in toluene (250 mL) at room temperature. The mixture was stirred at 100° C. under argon atmosphere for 16 hours. The mixture was filtrated through celite. The filtrate was extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (24.8 g).

Quelle