Is it possible to synthesize para-aminoguanidylphenol in this way? What are the conditions for interaction?
Phenol has pKa of ~ 10.0 while p–bromophenol has pKa of less than 9.35 which indicates an increased acidity compared to phenol. When a halogen is attached to a benzene ring, it is difficult to undergo nucleophilic substitution & other substitutions.
Aminoguanidine bicarbonate has the structure HN=C(NH2)(NHNH2).H2CO3 so the chemist will expect an acid-base reaction of p–bromophenol with the –NH2 groups but the presence of the carbonate part will not help this reaction because it is weakly acidic.
I do not think that it is possible to obtain para-aminoguanidylphenol since (Br) cannot be replaced & if there is an interaction, then it will be a weak one on the 2 amino sites.
Aromatic guanidines are usually synthesise by reacting aniline with cyanamide or thioureas. See this link for some references:
https://www.organic-chemistry.org/synthesis/C1N/guanidines.shtm
Starting with 4-bromophenol will most likely mean converting to an appropriate amine. 4-aminophenol may possibly be used with protection of the phenol.
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