Potassium Iodide → 3-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

Participants

Reaction Steps

A solution of 3-fluoro-4-nitrophenol (50.0 g, 0.31 mol), 3-(chloromethyl)-1-methyl-1H-pyrazole hydrochloride (52.1 g, 0.31 mol), powdered potassium carbonate (53.3 g, 0.38 mol), potassium iodide (52.8 g, 0.32 mol), and acetonitrile (900 mL) was stirred at 60° Celsius for 8 h. The reaction was cooled to RT and concentrated to dryness. The residue was partitioned between H2O (500 mL), sat. NaHCO3 (200 mL), and ethyl acetate (900 mL). The organic layer was separated, dried with MgSO4, filtered and concentrated to dryness. The resulting residue was recrystallized from ethanol (250 mL) and H2O (250 mL). The solid was collected by filtration and rinsed with a H2O/ethanol (2:1, 225 mL) followed by hexanes (250 mL) yielding the title compound as a tan solid (70.7 g, 90.2%). MS (ESI): mass calcd. for C11H10FN3O3, 251.1; m/z found, 252.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.13-8.03 (m, 1H), 7.42-7.32 (d, J=2.2, 1H), 6.93-6.87 (m, 1H), 6.87-6.84 (d, J=1.6, 1H), 6.36-6.29 (d, J=2.2, 1H), 5.18-5.10 (s, 2H), 4.00-3.87 (s, 3H).

Provenance & Evidence