Morpholine → HCID 57422999, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 5-bromo-2-chloro-4-methoxybenzoate (1.486 g, 5.32 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.132 g, 0.21 mmol), palladium(II) acetate (0.024 g, 0.11 mmol) and cesium carbonate (2.425 g, 7.44 mmol) were mixed together and evacuated then purged with nitrogen. Toluene (10 mL) and morpholine (0.464 mL, 5.32 mmol) were added and the mixture evacuated and purged with nitrogen several times. The suspension (red) was heated to 100 °C for 18 hours under nitrogen. The mixture was allowed to cool to ambient temperature and filtered, washing with EtOAc. The filtrate was concentrated to provide an orange residue. The crude product was purified by flash silica chromatography, elution gradient 0 to 35% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-chloro-4-methoxy-5-morpholinobenzoate (0.826 g, 54.4 %) as a cream crystalline solid. Lower than expected yield (previously recorded 80% EN04398-06).....not sure what has happened.

Provenance & Evidence