Morpholine → 4-(2-Fluoro-4-nitrophenyl)morpholine

Participants

Reaction Conditions

Reaction Steps

A suspension of morpholine (4.72 mL, 4.72 g, 54.2 mmol) and dibasic potassium phosphate (9.44 g, 54.2 mmol) in DMSO (27 mL) was treated with 3,4-difluoronitrobenzene (3.0 mL, 4.31 g, 27.1 mmol) was warmed at 60° C. for 18 h. The solution was cooled and diluted with ethyl acetate and extracted with water (3×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded the title compound (6.32 g, ca. 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.00 (ddd, J=9.0, 2.6, 0.9 Hz, 1 H), 7.92 (dd, J=13.1, 2.6 Hz, 1 H), 6.92 (t, J=8.8 Hz, 1 H), 3.88 (m, 4 H), 3.29 (dd, J=5.5, 4.0 Hz, 4 H). MS +DCI m/z (rel abundance) 227 (10, M+H), 244 (100, M+NH4).

Provenance & Evidence