4-Bromobiphenyl → HCID 58400034, compound

Participants

Reaction Steps

0.35 g (1.58 mmol) of Pd(OAc)2 and 4.8 ml (4.86 mmol) of tri-tent-butyl-phosphine (1 M solution in toluene) are added to 660 ml of degassed toluene, and the mixture is stirred for 5 min. 37.2 g (160 mmol) of 4-bromobiphenyl, 29.4 g (160 mmol) of N-phenyl-o-phenylenediamine and 22.4 g (233 mmol) of sodium tert-butoxide are then added to the solution, which is then degassed and stirred for 10 h at 140° C. under a protective-gas atmosphere. After the solution has cooled, 200 ml of NH4Cl solution and 50 ml of ethyl acetate are added, the phases are separated, washed with water, dried over MgSO4 and evaporated. The solid is dissolved in toluene and filtered off via Celite. The crude product is washed by stirring with hot heptane and washed with MeOH, giving 47 g (140 mmol) of a crystalline solid. The overall yield is 80%.

Provenance & Evidence