Nitric Acid → Chlorofluoronitroacetic Acid

Participants

Reaction Steps

The yield of chlorofluoronitroacetic acid in the nitration reaction was increased to 44% by replacing sulfuric acid with oleum. When a mixture of oleum, nitric acid and trifluoracetic acid was reacted with 1,2-dichlorodifluoroethylene, chlorofluoronitroacetic acid was obtained in 63% yield along with 14% of the 1,2-addition product, 1,2-dichloro-1,2-difluoro-2-nitroethyl trifluoroacetate, bringing the total yield of the nitration reaction to 77%. Apparently the 1,2-addition product was formed first and then was hydrolyzed in situ, to give the acetic acid derivative. The lower boiling point and diminished water sensitivity of the 1,2-addition product makes it a potentially attractive alternative to chlorofluoronitroacetic acid in subsequent nitration reactions.

Provenance & Evidence