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

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Reaction Steps

To sodium hydride (303 mg) under an argon atmosphere at 0° C. was added dropwise 2,2,2-trifluoroethanol (775 μl) and the mixture was then stirred at RT for 90 min. A solution of 2,5-dibromopyrimidine (1.5 g) in DMF (8 ml) was then added and stirring continued at RT for 2 hours. The reaction mixture was poured into ice (50 mL) and extracted with EtOAc (2×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo to afford 5-bromo-2-(2,2,2-trifluoro-ethoxy)-pyrimidine (790 mg, 49%) as a yellow oil which was used in the next step without further purification. MS (EI): 258 ([{81Br}M]+), 256 ([{79Br}M]+), 189 ([{81Br}M−CF3]+), 187 ([{79Br}M−CF3]+).

Provenance & Evidence