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3-Bromopyridine undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, involved in formation of the Grignard by Mg exchange with i-PrMgCl and in transmetallation of the lithiated derivative with zinc chloride followed by treatment with an electrophile as a route to 4-substituted 3-bromopyridines.
Jennifer A. Love Dr.; John P. Morgan.;Tina M. Trnka.;Robert H. Grubbs Prof. A Practical and Highly Active Ruthenium-Based Catalyst that Effects the Cross Metathesis of Acrylonitrile. Angewandte Chemie International Edition. 2002, 41 (21), 4035-4037.
Wenjie Li.; Dorian P. Nelson.; Mark S. Jensen.; R. Scott Hoerrner.; Dongwei Cai.; Robert D. Larsen.; Paul J. Reider. An Improved Protocol for the Preparation of 3-Pyridyl- and Some Arylboronic Acids. J. Org. Chem. 2002, 57 (16), 5394-5397.
Undergoes lithiation with LDA at low temperatures in the 4-position: Heterocycles, 35, 151 (1993). Formation of the Grignard by Mg exchange with i-PrMgCl: Tetrahdron Lett., 40, 4339 (1999). Transmetallation of the lithiated derivative with ZnCl2 followed by treatment with an electrophile has been described, as a route to 4-substituted 3-bromopyridines: Org. Lett., 3, 835 (2001).
Hazard Statements: H227-H302-H311-H332-H315-H319-H335
Combustible liquid. Harmful if swallowed. Toxic in contact with skin. Harmful if inhaled. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P280h-P305+P351+P338-P309-P310a
Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: