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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2378536Generated: November 3, 2026

Cesium carbonate → Methyl 3-(3-bromo-4-phenoxyphenyl)propionate

https://huagongshe.com/reaction/2378536

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantIodobenzeneHCID 11575—
Reactant2,2,6,6-Tetramethyl-3,5-heptanedioneHCID 70700—
ReactantMethyl 3-(3-bromo-4-hydroxyphenyl)propanoateHCID 22558720—
CatalystCuprous chlorideHCID 62652—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Solventtert-Butyl methyl etherHCID 15413—
ProductMethyl 3-(3-bromo-4-phenoxyphenyl)propionateHCID 68742079—

Reaction Conditions

Temperature120 °C

Reaction Steps

A solution of Intermediate 5 (3.08 g) in anhydrous N-methylpyrrolidone (9.5 ml, WAKO) was successively added with cesium carbonate (3.58 g, WAKO), iodobenzene (1.4 ml, TCI), dipivaloylmethane (0.12 ml, TCI) and copper(I) chloride (275 mg, WAKO), and stirred 120° C. for 16 hours under argon gas atmosphere. The reaction mixture was added with t-butyl methyl ether (25 ml), and insoluble solids were removed by filtration. The filtrate was washed successively with 2 N aqueous hydrochloric acid and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane:ethyl acetate=1:10) to obtain the title compound (Compound No. A-31, 1.00 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07470807B2
Source datasetuspto-grants-2008_12
ORD IDord-1766ff505ee64f6e8e9af941fc52e333
Source noteuspto-grants-2008_12