873387-30-5Relevant academic research and scientific papers
Halophenol rearrangement in Lewis acid-catalyzed Friedel-Crafts conditions: Evidence of competitive initial protonation and acylation
Saha, Koushik,Lajis, Nordin H.,Abas, Faridah,Naji, Nabil Ali,Hamzah, A. Sazali,Shaari, Khozirah
, p. 821 - 825 (2008)
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. CSIRO 2008.
