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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1662339Generated: October 25, 2026

Methyl iodide → Methyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoate

https://huagongshe.com/reaction/1662339

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantCesium carbonateHCID 10796—
Reactant4-Bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acid 4-bromo-3-(tetrahydro-2H-pyran-2-yloxy)benzoic acidHCID 67429525—
SolventAcetoneHCID 180—
SolventWaterHCID 962—
ProductMethyl 4-bromo-3-(tetrahydropyran-2-yloxy)benzoateHCID 16747841100%

Reaction Steps

To flask containing 26.1 (2.15 g, 7.14 mmol) and cesium carbonate (3.95 g, 12.1 mmol) in acetone (50 mL), was added iodomethane (0.667 mL, 10.7 mmol). The resulting mixture was stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/Hexanes) to provide methyl 26.2 (2.25 g, 99% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08030354B2
Source datasetuspto-grants-2011_10
ORD IDord-8bf91a6cce7a4ce999e9addf49610b4a
Source noteuspto-grants-2011_10