Sodium Carbonate → HCID 22647396, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-(4-Bromo-2,6-dimethyl-phenoxy)-pyridine 1-oxide (14, 10 g, 34 mmol, 1 equiv) and Na2CO3 (3.6 g, 34 mmol, 1 equiv) in POCl3 (100 mL) was heated to 105° C. for 30 h. The reaction was cooled to RT and the POCl3 was removed by rotary evaporation. The residue was dissolved in EtOAc and partioned into a chilled biphasic solution of EtOAc and 1 N NaOH. The aqueous layer was treated with NaOH (s) until the pH >1. The aqueous layer was extracted with EtOAc (3×), and the combined organics were washed with brine, dried (MgSO4) and concentrated. Recrystallization (EtOH) provided the desired material as off-white crystals (73%). 1H NMR (300 MHz, CDCl3) δ8.21 (d, J=6.2 Hz, 1H), 7.28 (s, 2H), 6.66 (m, 2H), 2.10 (s, 6H). 13C NMR (100 MHz, CDCl3) δ165.6, 153.5, 151.3, 149.0, 133.3, 132.5, 119.6, 110.7, 110.2, 16.4.

Provenance & Evidence