3-Bromo-4-chloropyridine → 3-Bromo-4-(2,5-difluoro-4-nitrophenoxy)pyridine

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Reaction Conditions

Reaction Steps

2,5-Difluoro-4-nitro-phenol (1.739 g, 9.93 mmol) and 3-bromo-4-chloro-pyridine (0.637 g, 3.31 mmol) were dissolved in chlorobenzene (6 mL) and heated at 145° C. overnight. The solvent was removed under reduced pressure and the residue partitioned between EtOAc and 10% aqueous K2CO3. The mixture was extracted with EtOAc (2×), and the combined organic extracts were washed with 10% aqueous K2CO3 and brine, dried, evaporated and purified by silica gel chromatography (hexanes/EtOAc) to yield 3-bromo-4-(2,5-difluoro-4-nitrophenoxy)pyridine (414 mg, 38% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.84 (s, 1H), 8.51-8.45 (m, 2H), 7.82-7.78 (m, 1H), 7.22 (d, 1H); MS (ESI) m/z: 331.0 (M+H+).

Provenance & Evidence