p-Fluoronitrobenzene → Nitrobenzene

Yet another alternative strategy for the formation of calixarene conjugates involves first derivatizing pre-calixarene monomers followed by the formation of a calixarene structure. For example, perfluoro-tert-butylphenol monomers may be prepared by reacting p-fluoro-nitrobenzene with Cs+C(CF3)3 -- in monoglyme to yield nitrobenzene, followed by reduction of the nitro group to an amino group, diazotization of the amino group to yield a diazonium salt, and hydrolysis to yield a hydroxy group. In the same manner that 4-tert-butylphenol is reacted with formaldehyde to yield a simple calixarene, 4-perfluoro-tert-butylphenol may be reacted with formaldehyde to yield a calixarene conjugate wherein the imaging moiety is perfluoro-tert-butyl (--C(CF3)3) in the 4-position.

ORD record

ord-176ab9697c0b4ef094522d7378f1a5e6

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05846515