Premium
Halogenation of [2‐(trimethylsilyl)ethoxy]methyl (SEM) protected 2,2′‐Bi‐ H ‐imidazole
Author(s) -
Matthews Donald P.,
Whitten Jeffrey P.,
Mccarthy James R.
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240328
Subject(s) - chemistry , trimethylsilyl , imidazole , alkoxy group , halogenation , yield (engineering) , medicinal chemistry , organic chemistry , alkyl , materials science , metallurgy
2,2′‐Bi‐1 H ‐imidazole, when protected with the [2‐(trimethylsilyl)ethoxy]methyl (SEM) blocking group, on treatment with N ‐bromosuccinimide or N ‐chlorosuccinimide yields predominantly the monohalogenated derivatives 4a and 4b. The [2‐(trimethylsilyl)ethoxy]methyl group is subsequently removed to yield pure mono‐halo‐2,2′‐bi‐ H ‐imidazoles 2 .