Phosphorus oxybromide → 4-Bromo-5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridine

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Reaction Conditions

Reaction Steps

To a mixture of 5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridin-4(1H)-one (100 mg, 0.400 mmol) in DCE (10 mL) was added phosphoryl tribromide (138 mg, 0.480 mmol). The mixture was stirred at 85° C. for 1 h. Then the mixture was added to aqueous NaHCO3 solution. The mixture was extracted with EA (50 mL×2). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford 4-bromo-5-nitro-2-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridine (60 mg, 0.096 mmol, 24.0% yield). TLC (PE/EA=10:1, Rf=0.6): 1H NMR (400 MHz, CD3OD): δ 8.74 (s, 1H), 6.83 (s, 1H), 1.54 (s, 6H). ES-LCMS m/z 312.9 (M+H).

Provenance & Evidence