Carbon Dioxide → 2-Bromo-5-fluoroisonicotinic acid

To a solution of 2-bromo-5-fluoropyridine (5.0 g) in tetrahydrofuran (100 mL) was 2.6 mol/L n-butyllithium tetrahydrofuran solution (12 mL) in a dropwise manner at −70° C., and this mixture was stirred at same temperature for 2 hours. To this reaction mixture was added excessive amounts of dry-ice at −70° C., and this mixture was stirred at room temperature for 12 hours. This mixture was poured into water, and this mixture was extracted with diethyl ether. To this obtained aqueous layer was added 1 mol/L hydrochloric acid (2 mL), and this mixture was extracted with ethyl acetate. This organic layer was concentrated to give the title compound (5.2 g).

1. customat −70° C.
2. stirringthis mixture was stirred at room temperature for 12 hours
3. extractionthis mixture was extracted with diethyl ether
4. additionTo this obtained aqueous layer was added 1 mol/L hydrochloric acid (2 mL)
5. extractionthis mixture was extracted with ethyl acetate
6. concentrationThis organic layer was concentrated

ORD record

ord-aed07b329ce247389bcf5940d9ea252d

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09023882B2