Methanol → Methyl 5-bromopyridine-2-carboxylate

Participants

Reaction Steps

To a 100 mL round bottle flask with 5-bromopicolinic acid (7.0 g, 35 mmol) in methanol (60 mL) was added dropwise thionyl chloride (3.0 mL) at ambient temperature. After addition the reaction mixture was heated to reflux for 3 h. Methanol was removed and ethyl acetate (80 mL) was added to the residue and was adjusted pH to 7.0 by addition of sodium bicarbonate solution. The organic phase was separated and dried over sodium sulfate. The organic solvent was removed and methyl 5-bromopicolinate 2 was obtained as a white solid which was used for the next step of the reaction without further purification. Yield: 6.57 g, 86.9%.

Provenance & Evidence