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

To a solution of triphenylphosphine (24.29 g, 92.6 mmol) in THF (dry, 160 mL) was added DIAD (18.23 mL, 92.6 mmol) dropwise at 0° C. under N2. After addition of DIAD, a solution of 1-(2,6-dichloro-3-fluorophenyl)ethanol (13.35 g, 63.86 mmol) and 3-hydroxy-2-nitropyridine (10.29 g, 73.44 mmol) in THF (anhydrous, 160 mL) was added dropwise. The ice-bath was removed and the reaction mixture was allowed to warm to room temperature and stirred at room temperature for 4 hrs. The reaction mixture was concentrated by evaporator to give a yellow residue. A saturated solution of NH4Cl (200 mL) was added. The aqueous phase was extracted with EtOAc (3×150 mL). The combined organic phase was washed with brine (2×80 mL), dried over anhydrous Na2SO4, concentrated by evaporation in vacuo to give a yellow residue which was purified by CombiFlash (220 g silica gel column, Hexane/EtOAc) to afford (±)-3-(1-(2,6,-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (21.1 g, 100%) as a white solid.

1. customThe ice-bath was removed
2. concentrationThe reaction mixture was concentrated by evaporator
3. customto give a yellow residue
4. extractionThe aqueous phase was extracted with EtOAc (3×150 mL)
5. washThe combined organic phase was washed with brine (2×80 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated by evaporation in vacuo
8. customto give a yellow residue which
9. customwas purified by CombiFlash (220 g silica gel column, Hexane/EtOAc)

ORD-Eintrag

ord-a2ecf4d52c2c47388b14afcbde413e15

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09226923B2