Dichlorodiphenylsilane → HCID 90386979, compound

Participants

Reaction Conditions

Reaction Steps

N-(3-(9H-carbazol-9-yl)phenyl)-2-bromo-N-(2-bromophenyl)aniline (4.05 g, 7.13 mmol) was added into a 250-mL round bottom flask and solubilized in dry THF (100 ml). The mixture was cooled down to −78° C. Butyllithium (5.70 ml, 14.25 mmol) was added dropwise. The mixture was stirred at −78° C. for 2 hours. Dichlorodiphenylsilane (1.467 ml, 7.13 mmol) was then added dropwise. The mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with water, extracted three times with diethyl ether and washed three times with water. The crude material was purified by column chromatography using hexane and dichloromethane (85/15) as the eluent. After most of the impurities came out, the eluent was gradually changed to 25% dichloromethane in hexane. The white powder was then triturated in acetone and then recrystallized three times from dichloromethane and hexane. 1.5 g of 5-(3-(9H-carbazol-9-yl)phenyl)-10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasiline was sublimed to afford 1.4 g yield of 33%.

Provenance & Evidence