2,2,2-Trifluoroethanol → 3-Bromo-5-nitro-2-(2,2,2-trifluoroethoxy)pyridine

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Reaction Conditions

Reaction Steps

Sodium hydride (3.2 g, 80.02 mmol) was added carefully in small portions to 2,2,2-trifluroethanol (CAS Registry No. 75-89-8) (60 ml) at 0° C. under nitrogen atmosphere and stirred at 25° C. for 30 minutes. Then 3-bromo-2-chloro-5-nitropyridine (CAS Registry No. 5470-17-7) (2 g, 8.42 mmol) in trifluoroethanol was added, and the reaction mixture was refluxed for 16h. The solvent was evaporated in vacuo, and the residue was taken up in water and extracted with ethyl acetate (3×120 ml). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated to get the crude residue (3 g). The crude was purified by column chromatography (3% ethyl acetate/hexane) to give the desired product (2.4 g, 95%) as yellow liquid. MS (LC/MS): not responding, NMR is in agreement with the structure: 1H-NMR (400 MHz, CDCl3): δ 4.90 (m, 2H), 8.68 (d, 1H), 8.98 (d, 1H).

Provenance & Evidence