Dibenzofuran → dibenzofuran-4-yl(triphenyl)silane

Participants

Reaction Steps

Dibenzo[b,d]furan (5.00 g, 29.7 mmol) was dissolved in THF (150 mL), and cooled in the CO2/i-PrOH bath. n-Butyllithium solution in hexane (2.5 M, 12.49 mL, 31.2 mmol) was added dropwise by syringe. After addition, it was stirred at room temperature for 2 hours, and cooled again in the CO2/i-PrOH bath. Chlorotriphenylsilane (8.77 g, 29.7 mmol) in ether (50 mL) was added dropwise into the reaction solution. The reaction was gradually warmed to room temperature and stirred overnight. After evaporation of the solvent, the crude product was purified by column chromatography on silica gel with DCM/hexane (1/9, v/v) as eluent to yield dibenzo[b,d]furan-4-yltriphenylsilane (8.2 g, 65%) as a white solid.

Provenance & Evidence