Reaktion #490326

Reaktionsgleichung

dibenzo[b,d]thiophen-4-boronic acid

bis(3-bromophenyl)diphenylsilane

potassium carbonate

→

(3-bromophenyl)(3-(dibenzo[b,d]thiophen-4-yl)phenyl)diphenylsilane

Ausbeute 62.4%

Lösungsmittel

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction mixture was quenched with water
2. 2
   Extraktionextracted with DCM
3. 3
   Waschenwashed with brine and water
4. 4
   Trocknendried over Na2SO4
5. 5
   SonstigeUpon evaporation of the solvent
6. 6
   Sonstigethe residue was purified by column chromatography on silica gel with hexane:DCM (9.5:0.5 to 9:1
7. 7
   workup.DISSOLUTIONThe crude product was dissolved in DCM
8. 8
   Sonstigeprecipitated with methanol
9. 9
   Filtrationfiltered

Vorschrift

A mixture solution of dibenzo[b,d]thiophen-4-boronic acid (1.84 g, 8.04 mmol), bis(3-bromophenyl)diphenylsilane (9.97 g, 20.17 mmol), Pd(PPh3)4 (0.19 g, 0.16 mmol) and potassium carbonate (6.69 g, 48.4 mmol,) in toluene (60 mL) and water (20 mL) was heated at 100° C. under nitrogen overnight. After cooling to room temperature, the reaction mixture was quenched with water, extracted with DCM, washed with brine and water, and dried over Na2SO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (9.5:0.5 to 9:1, v/v) as eluent. The crude product was dissolved in DCM, precipitated with methanol, and filtered to yield (3-bromophenyl)(3-(dibenzo[b,d]thiophen-4-yl)phenyl)diphenylsilane (3.0 g, 62%) as a white solid.

Quelle