Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
Koushik, Saha and Lajis, Md Nordin and Abas, Faridah and Ali Naji, Nabil and Hamzah, A. Sazali and Shaari, Khozirah (2008) Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation. Australian Journal of Chemistry, 61 (10). pp. 821-825. ISSN 0004-9425
Official URL: http://dx.doi.org/10.1071/CH08084
Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all.
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