반응 #43939

반응 방정식

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

수율 70.0%

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

수율 70.0%

용매

ethyl acetate

water

toluene

water

반응 조건

후처리

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

실험 절차

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.

출처