Morpholine → 4-(3-Chloro-5-nitrophenyl)morpholine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-3-chloro-5-nitrobenzene (4.5 g, 19.03 mmol), morpholine (1.7 mL, 19.03 mmol), sodium tert-butoxide (3.11 g, 32.4 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.87 g, 0.952 mmol), XPhos (0.91 g, 1.903 mmol), and toluene (40 mL) was stirred at 100° C. under nitrogen for 2 h, then filtered through Celite and concd. The resulting residue was partitioned between EtOAc and water, and the organic phase was washed with satd aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concd. Purification by column chromatography (silica; 0-25% EtOAc in hexanes) afforded 4-(3-chloro-5-nitrophenyl)morpholine as a yellow amorphous solid. Mass Spectrum (ESI) m/e=243.0 (M+1).

Provenance & Evidence