2-Bromo-5-nitroanisole → 2-(2-Methoxy-4-nitrophenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-bromo-2-methoxy-4-nitrobenzene (7 g, 30.17 mmol), bromo(pyridin-2-yl)zinc (80 mL of 0.5M in THF, 40 mmol), tetrakis(triphenlyphosphine)palladium(0) (1.7 g, 1.47 mmol) in 70 mL THF was degassed with nitrogen for 10 minutes, then heated at 63° C. for 6 hr. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude purified by liquid chromatography on silica (EtOAc/Hexane 3/7) to give 2-(2-methoxy-4-nitrophenyl)pyridine. MS (ESI) 231 (M++H).

Provenance & Evidence