Reaktion #43939

Reaktionsgleichung

3-Bromo-4-phenoxybenzaldehyde

{2,6-dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acid

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

tripotassium phosphate

→

title compound

Ausbeute 70.0%

2′,6′-dimethyl-4′-[3-(methylthio)propoxy]-6-phenoxybiphenyl-3-carbaldehyde

Ausbeute 70.0%

Lösungsmittel

ethyl acetate

water

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool
2. 2
   Filtrationthe insoluble substance was filtered off through celite
3. 3
   WaschenThe organic layer of the filtrate was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80)

Vorschrift

3-Bromo-4-phenoxybenzaldehyde (1.11 g, 4.00 mmol), {2,6-dimethyl-4-[3-(methylthio)propoxy]phenyl}boronic acid (1.02 g, 4.00 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.263 g, 0.640 mmol) and tripotassium phosphate (1.70 g, 8.00 mmol) were dissolved in a mixed solvent of toluene (20 mL) and water (4 mL). After argon substitution, tris(dibenzylideneacetone)dipalladium(0) (0.147 g, 0.160 mmol) was added. The reaction mixture was stirred at 100° C. for 18 hr under argon atmosphere. The reaction mixture was allowed to cool, and water was added. The mixture was diluted with ethyl acetate, and the insoluble substance was filtered off through celite. The organic layer of the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-20:80) to give the title compound (1.13 g, yield 70%) as a yellow oil.

Quelle