Tetrahedron Letters p. 1559 - 1562 (1997)
Update date:2022-08-17
Topics:
Mongin, Florence
Schlosser, Manfred
Lithium diisopropylamide deprotonates ortho- and para-bromochlorobenzene randomly at the two halogen adjacent positions. Obviously for steric reasons, the bulkier base lithium 2,2,6,6-tetramethylpiperidide favors the attack in the vicinity of the chlorine rather than the bromine atom to the extent of 2:1. At -75°C, both 2-bromo-3-chlorophenyllithium and 3-bromo-2-chlorophenyllithium isomerize to give 2-bromo-6-chlorophenyllithium. The latter species can be directly generated from 1-bromo-3-chlorobenzene.
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