Reaktion #490327

Reaktionsgleichung

2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

bis(3-bromophenyl)diphenylsilane

SPhos

K3PO4

→

(3-bromophenyl)(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)diphenylsilane

Ausbeute 30.6%

Lösungsmittel

xylene

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 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.0 g, 15.53 mmol), bis(3-bromophenyl)diphenylsilane (19.19 g, 38.8 mmol), Pd2(dba)3 (0.28 g, 0.31 mmol), SPhos (0.26 g, 0.62 mmol) and K3PO4 (3.30 g, 15.53 mmol) in xylene (150 mL) and water (15 mL) was refluxed under nitrogen at 120° C. 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)-[1,1′-biphenyl]-3-yl)diphenylsilane (3.2 g, 30.6%) as a white powder.

Quelle