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

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-bromo-2-methoxy-4-nitro-benzene (2.5 g, 10.8 mmol), Pd2(dba)3 (0.124 g, 0.215 mmol), NaOt-Bu (1.55 g, 16.2 mmol) and BINAP (0.202 g, 0.323 mmol) in toluene (20 mL) at 20° C. was added morpholine (1.5 mL, 17.2 mmol) over 10 min. The mixture was stirred at 80° C. for 3 h when TLC indicated no starting material remained, at which time the mixture was evaporated under reduced pressure followed by the addition of H2O (50 mL). CH2Cl2 extraction (3×15 mL), followed by drying of the combined organic layers with MgSO4 afforded, after filtration and concentration, an orange oil. Chromatography on silica gel (97:3 CH2Cl2/MeOH) yielded pure compound.

Provenance & Evidence