On the synthesis of 2-amino-4,6-difluorobenzonitrile: Highly selective formation of 5-fluoro-3-nitro-1,2-benzoquinone 2-diazide in the attempted Sandmeyer cyanation of 2,4-difluoro-6-nitrobenzenediazonium cation

摘要

Attempted cyanation of a diazonium salt derived from 2,4-difluoro-6-nitroaniline gives 5-fluoro-3-nitro-1,2-benzoquinone 2-diazide double dagger in good yield by selective nucleophilic substitution of the 2-fluoride group by hydroxide, instead of the desired 2-amino-4,6-difluorobenzonitrile, which can be obtained by the reaction of 2,4,6-trifluorobenzonitrile with ammonia. [References: 7]