Dichloromethane → HCID 58084636, compound

Participants

Reaction Steps

A mixture of 9H-carbazole (10 g, 59.8 mmol), 4-bromodibenzo[b,d]thiophene (18.89 g, 71.8 mmol), and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.982 g, 2.392 mmol) in 200 mL of Xylene was bubbled with N2 for 20 min. Pd2dba3 (0.548 g, 0.598 mmol) and sodium 2-methylpropan-2-olate (8.62 g, 90 mmol) were then added, and the mixture was heated to reflux under N2 for 24 h. TLC indicated the reaction did not go to completion. 0.3 g of Pd2(dba)3 and 0.6 g of dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine was added. The reaction was continued to reflux. The reaction was monitored by GC. After another 24 h, there was still carbazole starting material remaining. Again, 0.3 g of Pd2(dba)3 and 0.6 g of dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine were added. The reaction was refluxed again for 24 h. The reaction was stopped and worked up for purification. Column was used for purification. (1:3 dichloromethane:hexanes) 10 g (47.8% yield) of product was obtained.

Provenance & Evidence