Reacción #516564

Ecuación de reacción

diethylmethoxyborane

water

n-butyl lithium

3-bromopyridine

→

diethyl(3-pyridyl)borane

Rendimiento 76.8%

Disolventes

brine

butyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 16 h
2. 2
   Otroseparated organic layer
3. 3
   Secadodried over sodium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   workup.DISSOLUTIONThe resulting slurry was dissolved in isopropanol (500 ml)
6. 6
   Temperaturacooled
7. 7
   Otrothe product isolated by filtration

Procedimiento

Into a solution of n-butyl lithium (165 ml, 264 mmol) in butyl ether (250 ml) at −78 degrees under nitrogen was added 3-bromopyridine (25.4 ml, 264 mmol). After 1 h, added diethylmethoxyborane (52 ml, 396 mmol). The mixture was allowed to warm to room temperature. After 16 h, added water and brine, separated organic layer, dried over sodium sulfate, then concentrated. The resulting slurry was dissolved in isopropanol (500 ml), cooled and the product isolated by filtration give diethyl(3-pyridyl)borane (29.8 g).

Fuente