5-Fluoro-2-nitrophenol → 4-(2-(5-Fluoro-2-nitrophenoxy)ethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 2-morpholinoethyl methanesulfonate (1.5 g, 6.9 mmol), 5-fluoro-2-nitrophenol (0.99 g, 6.3 mmol), cesium carbonate (4.0 g, 12 mmol) and DMA (100 mL), and the reaction mixture was heated to 90° C. for 15 hours. Ethyl acetate (200 ml) was added to the cooled reaction mixture and the mixture was extracted with water (2×100 ml), 1N sodium hydroxide (2×50 ml) and aqueous 5% lithium chloride (2×50 ml). The organic solvent was removed on a rotary evaporator under reduced pressure. Purified of the crude product by silica column chromatography using 50:50 ethyl acetate:hexanes as eluant gave 0.71 g of 4-(2-(5-fluoro-2-nitrophenoxy)ethyl)morpholine (39% yield). EI (MS): 271 (MH+).

Provenance & Evidence