3-Cyanopyridine → 3-(3-Fluorobenzoyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromofluorobenzene (25.0, 0.143 mol) in ether (250 ml) was cooled to -78° C. and stirred during the dropwise addition of a 2.3 M solution of tert-butyllithium in pentane (62 ml, 0.143 mol). After the addition was completed, stirring was continued for 15 minutes and a solution of 3-cyanopyridine (14.9 g, 0.143 mol) in ether (125 ml) was added dropwise. The resulting mixture was allowed to warm to 15° C. and a solution of 12 N HC1 (36 ml) in H2O (90 ml) was added dropwise. After the resulting light yellow solution had stirred for 30 minutes, 10% NaOH was added to give a pH of 10, and the ether layer was separated. The aqueous phase was extracted twice with ether, the combined ether extracts were concentrated and the residue was distilled to yield 21.3 g (74%) of 3-(3-fluorobenzoyl)pyridine bp: 112°-128° C./59.99 Nm-2.

Provenance & Evidence