Carbon Dioxide → 3-Fluoropyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,4-diazabicyclo[2.2.2]octane (1.15 g, 10.3 mmol) in diethylether (50 ml) is added n-butyllithium (2.6M in hexane) (3.95 ml, 10.3 mmol) at −78° C. The reaction mixture is stirred at −20° C. for 1 h followed by the addition of a solution of 3-fluoro-pyridine (1.00 g, 10.29 mmol) in diethylether (30 ml) at −78° C. The yellow suspension is stirred at −60° C. for 1 h and then cooled to −78° C. followed by the addition of excess dry ice. The resulting solution allowed to warm to to −10° C. over 20 min. The precipitate is filtered and the residue is washed with ether which yields pure 3-fluoro-pyridine-2-carboxylic acid (1.20 g, 8.51 mmol, 83%).

Provenance & Evidence