Reaktion #1136621

Reaktionsgleichung

2-(benzyloxy)-5-bromobenzaldehyde

(2-fluoro-5-methoxyphenyl)boronic acid

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

sodium carbonate

→

title compound

Ausbeute 69.2%

4-(benzyloxy)-2′-fluoro-5′-methoxy-[1,1′-biphenyl]-3-carbaldehyde

Ausbeute 69.2%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with saturated brine
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To a solution of 2-(benzyloxy)-5-bromobenzaldehyde (5.00 g) in toluene (70 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (4.40 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (710 mg), tris(dibenzylideneacetone)dipalladium(0) (790 mg) and 2.0M aqueous sodium carbonate solution (25.8 mL) at room temperature, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.00 g) as orange crystals.

Quelle