Morpholine → Methyl 3-bromo-4-morpholinobenzoate

Reaction equation

C1COCCN1.COC(=O)c1ccc(I)c(Br)c1>CC(=O)O.CC(=O)O.COCCOC.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>COC(=O)c1ccc(N2CCOCC2)c(Br)c1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 3-bromo-4-iodobenzoate (1.981 g, 5.81 mmol) in DME (10 mL) were morpholine (0.559 mL, 6.39 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.362 g, 0.58 mmol), Palladium acetate (0.130 g, 0.58 mmol) and CESIUM CARBONATE (3.79 g, 11.62 mmol) added. The mixture was heated in the microwave oven for 12h at 110°C. The solids were filtered off through celite, the solvent was evaporated and the crude product was added to a silica gel column, 0-30% EtOAc in heptane yielding methyl 3-bromo-4-morpholinobenzoate (0.566 g, 32.5 %)