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

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%).

1. stirringstirred the reaction mixture for 2 h at RT
2. concentrationThe reaction mixture is concentrated under reduced pressure to and the mixture
3. additionwas poured in to ice cold water (20 mL)
4. extractionextracted with dichloromethane (2×50 mL)
5. washThe combined organic layer was washed with water, brine and solvent
6. customwas evaporated under reduced pressure

ORD record

ord-dfc2490eb4234ffea464552096f5155a

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163020B2