2,2,2-Trifluoroethanol → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidine

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Reaction Steps

A mechanically stirred slurry of 5-bromo-2-(methanesulfonyl)pyrimidine (24 g, 0.10 mol), trifluoroethanol (15 g, 0.15 mol), and potassium carbonate (28 g, 0.20 mol) in acetonitrile (250 mL) was heated at 70° C. for 12 hours. HPLC analysis indicated complete conversion. The solids were removed by filtration, and rinsed well with acetonitrile. The solvent was removed in vacuo and the residue partitioned between ether (50 mL) and water (25 mL). The aqueous phase was extracted with ether (2×25 mL), the organic layers combined, and washed with brine. Dried (Na2SO4), filtered, and solvent removed in vacuo, affording product as a pale yellow liquid, 19 g, 74 percent yield.

Provenance & Evidence