Morpholine → 4-(2-Methoxy-5-nitrophenyl)morpholine

Participants

Reaction Conditions

Reaction Steps

2-Bromo-1-methoxy-4-nitro-benzene (810 mg, 4 mmol), morpholine (420 μL, 4.8 mmol), cesium carbonate (1.8 g, 5.6 mmol), Pd2(dba)3 (75 mg, 0.02 mmol) and BINAP (75 mg, 0.03 mmol) were added to 5 mL dry dioxane under an argon atmosphere and heated to 80° C. for 6 hours. After cooling, the solvent was evaporated and the residue was purified by silica gel chromatagraphy (eluent: 5% MeOH/DCM) to afford 390 mg 4-(2-methoxy-5-nitro-phenyl)-morpholine (w): m/e: 238.09, MS (ES+): 239.3; 1H NMR (500 MHz, CDCl3): 8.0 (d, J=10 Hz, 1H), 7.8 (s, 1H), 6.9 (d, J=10 Hz, 1H), 4.1 (s, 3H), 3.9 (m, 4H) and 3.2 (m, 4H).

Provenance & Evidence