Phenylboronic Acid → 3-Bromo-5-phenylpyridine

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Phenylboronic acid (0.618 g, 5.065 mmol) is stirred in a mixture of DME (20 ml) and 2M Na2CO3 for 20 minutes. 3,5-dibromopyridine (1.0 g, 4.221 mmol) is added followed by PdCl2(Ph3P)2 (0.296 g, 0.4221 mmol) and the mixture is heated to 100° C. overnight. The DME layer is removed and is diluted with EtOAc, washing with 5M HCl (2×20 ml) then back extracted with EtOAc (70 ml). The acidic aqueous phase is basified with 6M NaOH (50 ml) and extracted with DCM (3×100 ml). The combined organic extracts are dried over MgSO4, filtered and evaporated to an oil which is stirred in iso-hexanes (15 ml) and the resulting solid is removed washing with a further 10 ml of iso-hexanes. Concentration of the organics in vacuo affords the title compound as a white solid MH+[235.74].

Herkunft & Nachweise