Sodium Carbonate → 3-Aminobiphenyl

Participants

Reaction Steps

To a solution of phenylboronic acid (10.5 g, 86.4 mmol) in 100 mL of MeOH, Na2CO3 (18.3 g, 172.2 mmol) and 3-bromoaniline (14.9 g, 86.4 mmol) were added sequentially. To the so obtained suspension, Pd(OAc)2 (500 mg, 2.16 mmol) was added and the reaction was heated to reflux of solvent until a black suspension appeared; the suspension was cooled at room temperature, diluted with MeOH and the black precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was splitted in water and CH2Cl2. The organic phase was dried on Na2CO3 and concentrated under reduced pressure to give 3-phenylaniline as a brown oil (14.6 g, yield 100%).

Provenance & Evidence