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

Participants

Reaction Steps

To suspension of 20 gm. (]42 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 1.6 M methyl lithium (360 mmoles) in ether over 1 hr. The reaction was stirred for an additional 2 hr., 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