Nitrogen → 6-Bromo-2,4'-bipyridine

Participants

Reaction Steps

Dry N2 was bubbled through a stirred solution of 2,6-dibromopyridine (1.6 gm, 6.7 mmole), pyridine-4-boronic acid (317 mg, 2.6 mmol), and Pd(PPh3)4 (160 mg) in aqueous 2M Na2CO3 (8 mL) and toluene (8 mL) at rt for 20 min. The reaction mixture was then heated to reflux for 10 hr. After cooling to rt CH2Cl2 (100 mL) was added and the mixture was washed with brine and dried (Na2SO4). Purification (Sio2, CH2Cl2/MeOH/NH4OH: 100/11/8) gave 6-bromo-[2,4′]bipyridine. MS (m/z): Calcd. C10H7N2Br (M+): 235, found: 234.9.

Provenance & Evidence