Phosphorus oxybromide → 2-Bromo-5-isopropylsulfanyl-pyridine

Participants

Reaction Conditions

Reaction Steps

DMF (5 mL) was added slowly to a stirred mixture of 5-isopropylsulfanylpyridin-2-ol (765.8 mg, 4.525 mmol) and POBr3 (5.189 g, 18.10 mmol) at ambient temperature. After 10 minutes, the reaction mixture was warmed to 95° C. for 1 hour. The reaction mixture was cooled to ambient temperature and quenched by the slow addition of ice. The aqueous layer was extracted with EtOAc (×3) and the combined organics washed with saturated aqueous NaHCO3 (×3), brine (×1), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion™, 80 g column, eluting with 0 to 20% EtOAc/Petroleum Ether, loaded in DCM) to give the sub-title product as an off-white solid (661 mg, 63% Yield, 65% purity). 1H NMR (400.0 MHz, DMSO) δ 1.24 (d, J=6.8 Hz, 6H), 3.58 (sept, 1H), 7.62 (d, J=8.0 Hz, 1H), 7.78 (dd, J=2.6, 8.4 Hz, 1H) and 8.37 (d, J=2.5 Hz, 1H) ppm; MS (ES+) 231.7.

Provenance & Evidence