p-Fluoronitrobenzene → 5-Ethyl-2-(2-(4-nitrophenoxy)ethyl)pyridine

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Reaction Steps

To a solution of 2-(5-ethyl-2-pyridyl)ethanol (12 g) and 4-fluoronitrobenzene (11.2 g) in dimethylformamide (80 ml) sodium hydride (3.9 g) is added portionwise under ice cooling. This mixture is agitated under ice cooling for one hour, at room temperature for thirty minutes, poured into ice water and extracted with ethyl acetate. Drying the organic layer and evaporating the solvent gives a yellow solid (4-(2-(5-ethyl-2-pyridyl)ethoxy)nitrobenzene, 21.4 g, 98.2%). Recrystallizing from a mixture of ether and hexane yields pale yellow crystals (m.p. 45–47° C.). NMR δ (ppm) in CDCl3: 1.25 (3H, t, J=7.6), 2.65 (2H, q, J=7.6), 3.28 (2H, t, J=6.7), 4.47 (2H, t, J=6.7), 6.95 (2H, m), 7.19 (1H, d, J=7.9), 7.49 (1H, dd, J=2.4; 8.0), 8.17 (2H, m), 8.41 (1H, d, J=2.2).

Provenance & Evidence