Isopropanol → 2-Bromo-6-isopropoxypyridine

Participants

Reaction Conditions

Reaction Steps

The compound was prepared in a manner similar to that described in WO 02/076983 (page 80). Dry isopropanol (25 mL, 42.2 mmole) was placed in an oven-dried 250 ml 3 necked flask under nitrogen, sodium spheres (0.5 g, 21.1 mmol) were added and the reaction was heated to 80° C. to dissolve the sodium. 2,6 dibromopyridine (10 g, 42.2 mmole) was added as a solid and the reaction was heated at 95° C. After heating for ˜2.5 hr the reaction was cooled and partitioned between ether and water. The organic layer was evaporated to give a solid plus oil, the mixture was suspended in hexanes, cooled, and filtered to remove the solid. The filtrate was evaporated carefully and chromatographed on silica eluting with hexanes to give the product as a clear, colorless oil.

Provenance & Evidence