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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 406Generated: October 28, 2026

Morpholine → Methyl 3-bromo-4-morpholinobenzoate

https://huagongshe.com/reaction/406

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
ReactantMethyl 3-bromo-4-iodobenzoateHCID 17750019—
ReagentCesium carbonateHCID 10796—
CatalystBinap, (A+-)-HCID 634876—
CatalystPalladium (II) acetateHCID 4144353—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductMethyl 3-bromo-4-morpholinobenzoateHCID 4482898832.45%

Reaction Conditions

Temperature110 °C

Reaction Steps

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 %)

Provenance & Evidence

Source dataset750 AstraZeneca ELN dataset
ORD IDord-41816b2f53f7429c8faade84ae4a9bb3
Source note750 AstraZeneca ELN dataset