Carbon Dioxide → 2-Fluoro-6-phenylpyridine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Cool a solution of LDA (3.46 mmol) in anhydrous tetrahydrofuran (6 mL) to −78° C. Cannulate the 2-fluoro-6-phenylpyridine in anhydrous tetrahydrofuran (6 mL) to the cooled LDA solution. Stir at −78° C. for 30 minutes then bubble carbon dioxide gas through the solution for 10 minutes. Allow the reaction to come to room temperature and purge with argon. Extract the reaction with 1M sodium hydroxide and discard the organics. Acidify the aqueous layer with conc. HCl and extract with ethyl acetate. Dry the organic layer over magnesium sulfate, filter and evaporate to yield the title compound as a light yellow solid (405 mg, 65%). MS (m/e): 216.1 (M−).

Provenance & Evidence