Water → Methyl 3-chloro-5-methoxypicolinate

Participants

Reaction Conditions

Reaction Steps

In a 1-L round bottom flask, the methyl 3-chloro-5-hydroxypicolinate (25.00 g, 133 mmol) and cesium carbonate (87 g, 267 mmol) were taken up in DMF (200 ml), and iodomethane (41.7 ml, 666 mmol) was added. A water-cooled condenser was attached, and the reaction vessel was heated in a 55° C. oil bath. After 3 h, the reaction was concentrated. The residue was taken up in 1.2 L of 80% EtOAc-hexane and 500 ml of brine. Not all the solids went in, so the mixture was filtered through Celite. The resulting filtrate's organic layer was separated, washed with brine (100 ml), dried over MgSO4 and concentrated. The residue was purified through silica gel using 30% to 40% EtOAc in hexane, affording 19.1 g (95 mmol) of a tan solid (71% yield). MS m/z=202 (M+H).

Provenance & Evidence