Phosphorus oxychloride → 2-Chloro-3-iodo-5-nitropyridine

Participants

Reaction Conditions

Reaction Steps

2-Hydroxy-3-iodo-5-nitropyridine (2.55g, 9.5 mmol), phosphorous pentachloride (2.60g, 12 mmol) and phosphorous oxychloride (2 mL) were combined in a flask under nitrogen and heated to 140° C. for 45 mins. The cooled reaction mixture was poured over ice to give a solid which was partitioned between CH2Cl2 and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was removed in vacuo to give compound 765B (2.25 g, 83%) as a yellow solid. HPLC: 98.5% at 2.75 min(YMC S5 ODS column) eluting with 1090% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm.

Provenance & Evidence