Iodine → HCID 13467546, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 18.5 g (0.761 mole) of magnesium turnings and several crystals of iodine in 800 ml of anhydrous ether, cooled in an ice bath and under an atmosphere of argon was slowly added a solution of p-bromofluorobenzene in 200 ml of ether. The solution was stirred for 2 hr at 25° C. and 97.02 g (0.530 mole) of 4-benzoylpyridine was added as a solid. An additional 1 liter of anhydrous ether was added, and the solution was stirred at 25° C. for 3 hr. The reaction mixture was poured into an icy, aqueous solution of ammonium chloride. The mixture stood in the hood overnight and a white solid was collected. The solid was dissolved in a mixture of methanol-methylene chloride. The solution was filtered and the solvent was removed in vacuo. The residue was crystallized from chloroform-hexane to give 66.86 g (45%) of title compound as a white, crystalline solid, m.p. 189°-192° C. Part of this was recrystallized from methylene chloride-acetonitrile-hexane, m.p. 190°-192° C.

Provenance & Evidence