Reaktion #3427

Reaktionsgleichung

3,5-dibromopyridine

phenylboronic acid

sodium carbonate

→

title compound

3-bromo-5-phenylpyridine

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux for 6 hours
3. 3
   Sonstigethe solvent was removed
4. 4
   SonstigeThe residue was purified by chromatography (silica gel
5. 5
   Wascheneluting with ether:hexane 1:10

Vorschrift

Portions of 3,5-dibromopyridine (1.0 g, 4.22 mmol), phenylboronic acid (570 mg, 4.6 mmol) and palladium tetra(triphenylphosphine) (60 mg) were combined in toluene (20 mL) with aqueous sodium carbonate solution (2M, 3.0 mL) and heated at reflux for 6 hours. The mixture was cooled to ambient temperature, and the solvent was removed. The residue was purified by chromatography (silica gel, eluting with ether:hexane 1:10 to give the title compound: MS (CI/NH3) m/z: 234/236 (M+H)+, 251/153 (M+NH4)+ ; 1H NMR (CDCl3, 300 MHz) δ7.21-8.02 (dd, J=2.0, 2.0 Hz), 8.65 (d, J=2.0 Hz), 8.75 (d, J=2.0 Hz).

Quelle