Nitric Acid → 5-Fluoro-2-nitrotoluene

Participants

Reaction Steps

A solution of 200 g of 3-fluorotoluene and 670 ml of concentrated nitric acid was heated at 50°-55° for 8 hours; after standing overnight, the reaction mixture was poured into 1200 ml of ice-water. The organic layer was separated, and the aqueous layer was extracted three times with ether; the organic fraction and the ethereal extracts were combined, washed once with water and saturated sodium chloride solution. The combined organic fraction was dried over magnesium sulfate, filtered, and evaporated under reduced pressure to give a yellow oil. This crude product was distilled using a 30-cm vacuum-jacketed column filled with glass helices to yield 192.7 g of 5-fluoro-2-nitrotoluene, bp 74.5°-77°/4 mm.

Provenance & Evidence