Triphenylphosphine → 3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

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Reaction Steps

1-(2,6-dichloro-3-fluorophenyl)ethanol (29.1 g, 139 mmol) and 3-hydroxy-2-nitropyridine (24.1 g, 153 mmol) were dissolved in anhydrous tetrahydrofuran (300 mL), and triphenylphosphine (PPh3, 51.1 g, 195 mmol) was added and the mixture was stirred for 1 h at room temperature. At 0° C., to the reaction liquid was added diisopropyl azodicarboxylate (DIAD, 38.4 mL, 195 mmol) dropwise. The resultant mixture was stirred overnight at room temperature. The resultant mixture was evaporated under reduced pressure to remove solvent, then purified via silica gel column chromatography (petroleum ether:ethyl acetate=3:1) to yield the target product as white crystals (41.2 g, 124 mmol; yield=89%).

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