Reaktion #800776

Reaktionsgleichung

CO2 i-PrOH

I2

CO2 i-PrOH

n-Butyllithium

hexane

Dibenzo[b,d]furan-4-yltriphenylsilane

→

(6-iododibenzo[b,d]furan-4-yl)triphenylsilane

Ausbeute 62.0%

Lösungsmittel

ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was warmed to room temperature
2. 2
   workup.STIRRINGstirred for 1 hour
3. 3
   Sonstigequenched with an aqueous solution of NaHSO3 (10 wt %, 100 ml)
4. 4
   workup.ADDITIONIt was diluted with saturated aqueous NaCl solution
5. 5
   Extraktionextracted with EtOAc (50 mL×3 times)
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   Sonstigethe solvent was evaporated
8. 8
   SonstigeThe residue was purified by column chromatography on silica gel with hexane/EtOAc (95/5 to 90/10

Vorschrift

Dibenzo[b,d]furan-4-yltriphenylsilane (9.80 g, 22.97 mmol) was dissolved in dry THF (100 mL) and cooled in the CO2/i-PrOH bath. n-Butyllithium in hexane (2.5 M, 12.87 mL, 32.2 mmol) was added dropwise. It was warmed to room temperature, stirred for 4 hours, and cooled again in the CO2/i-PrOH bath, and a solution of I2 (8.63 g, 34 mmol) in ether (50 mL) was added dropwise. The reaction mixture was warmed to room temperature, stirred for 1 hour, and quenched with an aqueous solution of NaHSO3 (10 wt %, 100 ml). It was diluted with saturated aqueous NaCl solution, extracted with EtOAc (50 mL×3 times). The organic extracts were combined, dried over anhydrous Na2SO4, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/EtOAc (95/5 to 90/10, v/v) as eluent to yield (6-iododibenzo[b,d]furan-4-yl)triphenylsilane (7.8 g, 62%) as a white solid.

Quelle