Ammonium Chloride → HCID 15020346, compound

Participants

Reaction Steps

A three-necked round bottom flask, equipped with a mechanical stirrer, flushed with nitrogen, and containing 3.74 g (0.154 mole) of magnesium turnings, was dried with a Bunsen burner. After the flask had cooled, 600 ml of tetrahydrofuran was added. To this mechanically stirred mixture was slowly added a solution of 29.4 g (0.152 mole) of 4-bromo-1,2-difluorobenzene in 50 ml of tetrahydrofuran. The mixture was stirred for 1 hour, and 45.11 g (0.13 mole) of (4-fluorophenyl)[1-(phenylsulfonyl)-4-piperidinyl]methanone was added as a solid. The solution was stirred at ambient temperatures for 3 hours and was poured into an icy aqueous solution of ammonium chloride. The aqueous mixture was extracted with methylene chloride, dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was recrystallized from methylene chloridehexane to give 58.89 g (82.9%) of the title compound. A small sample was recrystallized from a mixture of methylene chloride-ether-hexane to give an analytically pure sample of the title compound, mp 97°-99° C.

Provenance & Evidence