Pyridine → 3-Bromo-5-chlorobenzamide

Participants

Reaction Steps

To a solution of 3-bromo-5-chlorobenzoic acid (2.88 g; 12.2 mmol; Note 1) and pyridine (1.04 mL; 12.8 mmol) in MeCN (100 mL) at room temperature was added (Boc)2O (3.47 g; 15.9 mmol) in one portion. The mixture was aged 30 min, (NH4)2CO3 was added in one portion. After stirring approximately 16 h at room temperature, volatiles were removed in vacuo. The residue was partitioned between EtOAc/water and the layers were separated. The aqueous layer was extracted with EtOAc (×2), combined organics were washed (10% HCl, brine), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless solid. LC/MS (method A) tR 1.65 min; m/z 234, 236 (M+H, Br isotopes).

Provenance & Evidence