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Bromine-magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex Bu2PrMgLi: a new preparation methodology of functionalized picolines under noncryogenic conditions
Authors:Satoshi Kii  Takehiko Iida  Nobuyoshi Yasuda
Affiliation:a Process Research, Banyu Pharmaceutical Co. Ltd, 9-1, Kamimutsuna 3-Chome, Okazaki, Aichi 444-0858, Japan
b Merck Research Laboratories, Department of Process Research, PO Box 2000, Rahway, NJ 07065, USA
Abstract:The organomagnesium complex nBu2iPrMgLi, readily prepared from nBuLi and iPrMgCl (2:1), is quite efficient for the bromine-magnesium exchange of 5-bromo-2-picoline under noncryogenic conditions (at −10 °C). The resulting picolylmagnesium complex reacts with various electrophiles to afford functionalized picolines.
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