Methanol → Methyl 2,6-dichloro-5-fluoronicotinate

Participants

Reaction Steps

To a solution of 2,6-dichloro-5-fluoronicotinic acid (16) (5 g, 23.8 mmol) in methanol (50 ml) was added thionyl chloride in dropwise (5.66 g, 47.62 mmol) at 0° C. and 2 drops of DMF [vigourous bubbling was observed]. The mixture was stirred at room temperature for 3 h. To this methanol was added and stirred the reaction mixture for 2 h at RT. The reaction mixture is concentrated under reduced pressure to and the mixture was poured in to ice cold water (20 mL) and extracted with dichloromethane (2×50 mL). The combined organic layer was washed with water, brine and solvent was evaporated under reduced pressure to yield methyl 2,6-dichloro-5-fluoronicotinate (17) (5 g, 93.8%).

Provenance & Evidence