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Synthesis of Bromo‐iodo‐hydroquinone Monoalkyl Ethers
Author(s) -
Höger Sigurd
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719970139
Subject(s) - halogenation , chemistry , hydroquinone , iodine , phenols , organic chemistry , medicinal chemistry
Two methods for the preparation of 2‐bromo‐5‐iodo‐ p ‐alkoxyphenols and the isomeric 5‐bromo‐2‐iodo‐ p ‐alkoxyphenols are reported in detail. In both cases the key to successful synthesis is the use of the difference in ortho‐directing power of phenols, phenolethers and phenolesters. During the bromination of 2‐iodo‐4‐propyloxyphenyl acetate ( 5 ) an unexpected “iodo‐effect” was observed, which can be attributed to the high polarisibility of iodine.