Sodium Carbonate → 2-Chloro-4-(4-fluoro-2-methoxyphenyl)pyridine

Participants

Reaction Steps

To a solution of 4-fluoro-2-methoxyphenylboronic acid (440 mg, 2.58 mmol) in 8 ml of 1,4-dioxane was added 2.5 ml of saturated aqueous sodium carbonate solution. Argon gas was purged for 30 min at room temperature. 4-Bromo-2-chloropyridine (500 mg, 2.58 mmol) and tetrakis(triphenylphosphine)palladium (0) (150 mg, 0.129 mmol) were added to reaction mixture simultaneously and argon gas was bubbled for another 40 min. The reaction mixture was heated to reflux for 16 h, TLC confirms completion of reaction and the mixture was concentrated under reduced pressure. The residue was partitioned between DCM and water. The organic layer was separated, washed with brine, water, dried (Na2SO4) and concentrated. The obtained crude residue was purified through silica gel column chromatography eluting with 15% ethyl acetate in DCM to provide 2-chloro-4-(4-fluoro-2-methoxyphenyl)pyridine (450 mg, 73.3%).

Provenance & Evidence