Pyridine, hydrofluoride (1:1) → Methyl 5-fluoro-3-pyridinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 243 mg (1.6 mmol) of methyl 5-aminonicotinate in 5 mL of HF-pyridine at 0° C. was added 119 mg (1.72 mmol) of NaNO2. The mixture was stirred at 0° C. for 30 min. and at 50° C. for 1 h. The reaction was quenched by ice and sat. NaHCO3 solution. The aqueous layer was extracted with CHCl3, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1% MeOH/CHCl3) provided 139 mg of methyl 5-fluoronicotinate as a yellow solid in 56% yield.

Provenance & Evidence