p-Fluoronitrobenzene → 1-(2,2,3,3,4,4,4-Heptafluorobutoxy)-4-nitrobenzene

Participants

Reaction Steps

A solution of 2,2,3,3,4,4,4-heptafluorobutanol (5.7 g, 28.5 mmol) in DMF (100 mL) was stirred and cooled to −5° C. as sodium hydride (0.72 g, 30 mmol) was added. After 1 h at −5° C., the reaction was treated with 4-fluoronitrobenzene (4.1 g, 29 mmol). The reaction was allowed to warm to ambient temperature, concentrated, and slurried in methylene chloride (200 mL). The slurry was washed with an 1 N aqueous potassium hydroxide solution (2×) and brine solution, dried over basic alumina, treated with charcoal, filtered, and concentrated to give 4-(2′,2′,3′,3′,4′,4′,4′-heptafluorobutanoxy)nitrobenzene.

Provenance & Evidence