Potassium Fluoride → 4-Cyano-2-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

Treat a solution of 2-chloro-4-cyanopyridine (6.0 g, 43.5 mmol) and potassium fluoride (7.56 g, 130.3 mmol) in 1-methyl-2-pyrrolidinone (20 mL) with tetrabutylphosphonium bromide (14.8 g, 43.7 mmol) and heat to 100° C. for 18 hours. Dilute with water and extract with EtOAc. Wash EtOAc with water, brine, dry with Na2SO4, and concentrate to give the title compound (2.3 g, 43%). MS (ES) 123.1 (M+1)+. 1H NMR (400 MHz, CHCl3) δ 8.43 (d, 1H, J=5.2 Hz), 7.45 (m, 1H), 7.22 (m, 1H).

Provenance & Evidence