A NEW SYNTHESIS FOR 3-CHLORO-2,2',4,4',6,6'-HEXANITROBIPHENYL, PIPICL
NAVAL ORDNANCE LAB WHITE OAK MD
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3-Chloro-2,2,4,4,6,6-hexanitrobiphenyl, PIPICL, was prepared by a three-step procedure from picryl chloride and m-chloro- or m-bromoanisole. The first step involved the formation of m-picrylanisole by means of a mixed Ullmann reaction. Using 90 nitric acid and 30 oleum, the picrylanisole was nitrated to 3-methoxy-2,2,4,4,6,6-hexanitrobiphenyl which was in turn converted to PIPICL by treatment with pyridine and phosphorus oxychloride. When m- bromoanisole was used in the Ullmann reaction, the overall yield for the three steps was about 59. The use of m-chloroanisole resulted in a lower yield in the first step and an overall yield of about 52. Several variations in procedure are given for the preparation of m-picrylanisole.
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