1-Bromo-4-iodobenzene → HCID 86696082, compound

Participants

Reaction Steps

Toluene (125 mL) was bubbled with nitrogen gas for 15 minutes, and subsequently 1,1′-Bis(diphenylphosphino)ferrocene (0.2 g, 0.4 mmol) and Pd2(dba)3 (0.1 g, 0.1 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes, then N-phenyldibenzo[b,d]thiophen-4-amine (3.2 g, 11.6 mmol), 1-bromo-4-iodobenzene (4.5 g, 15.9 mmol), NaOtBu (1.5 g, 15.6 mmol) were added. The mixture was bubbled with nitrogen gas for 15 minutes and refluxed for 12 hours. After cooling, the reaction mixture was filtered through a silica pad and washed with 50% CH2Cl2/hexane. The solvent was removed in vacuo and the residue was purified by flash chromatography using 10-15% CH2Cl2/hexane to afford N-(4-bromophenyl)-N-phenyldibenzo[b,d]thiophen-4-amine (4.0 g, 80% yield) as a white solid.

Provenance & Evidence