Hydrofluoric Acid → 4-Fluoro-3,5-dimethylaniline

Participants

Reaction Conditions

Reaction Steps

The 95 ml. hexane solution of 3,5-dimethylphenylazide prepared in Step A above was charged to a rocker bomb and 20 ml. of hydrogen fluoride was added. The reaction mixture was then aged for 10 hours at room temperature with agitation, after which it was cooled, vented, and poured from the bomb, and the bomb rinsed with 40 ml. of water and 40 ml. of dichloromethane. The combined hexane, dichloromethane and hydrogen fluoride were blown down under nitrogen. The resulting residue was combined with the aqueous rinse, cooled to 0° C., and rendered alkaline with KOH pellets. The residue was then extracted three times with 75 ml. of dichloromethane per extraction, and the combined extracts dried over MgSO4 and then concentrated under reduced pressure to yield 7.34g. (66.2%) of a brown-red oil. This oil was then vacuum distilled at 40 mm. Hg to give 6.70g. of a colorless oil, a 60% yield. The final product had a b.p. of 127°-130° C. at 40 mm. Hg.

Provenance & Evidence