6-Fluoronicotinic Acid → 1-(6-Fluoropyridin-3-yl)ethan-1-one

Participants

Reaction Steps

To a suspension of 20 gm. (142 mmoles) of 2-fluoro-5-pyridinecarboxylic acid (J. Am. Chem. Soc., 71, 1125 (1949)) in 750 ml of ether, stirred and cooled in ice, was added 225 ml of 1.6M methyl lithium (360 mmoles) in ether over 1 hour. The reaction was stirred for an additional 2 hours, then 300 ml of ice water was added. The aqueous layer was washed with 2×100 ml fresh ether, acidified and extracted with ether to give 5.0 gm. (25%) of unreacted starting acid.

Provenance & Evidence