Tetrahydrofuran → 2-Bromo-6-phenylpyridine

Participants

Reaction Steps

To a solution of 2,6-dibromopyridine (2 g) in THF (100 mL) at -100° C. was added n-BuLi (6 mL of a 1.4M solution in hexane) over 10 min. After stirring for 20 min., ZnCl2 (17 mL of a 0.5M solution in THF) was added. The cold bath was removed and after 40 min., iodobenzene (0.94 mL) and tetrakis (triphenylphosphine) palladium (390 mg) were added and the mixture stirred at r.t. for 20 h. Ethyl acetate was added and the organics were washed with NaHCO3, H2O and brine, dried (MgSO4) and concentrated. Chromatography (silica gel; hexane/EtOAc (97:3)) provided the title compound as a solid.

Provenance & Evidence