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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1670719Generated: November 1, 2026

Citric Acid → 3-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

https://huagongshe.com/reaction/1670719

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCitric AcidHCID 311—
ReactantPotassium CarbonateHCID 11430—
ReactantMethyl 3-(bromomethyl)benzoateHCID 517981—
Reactant3-Bromo-5-ethoxy-4-hydroxybenzaldehydeHCID 612496—
CatalystTetrabutylammonium IodideHCID 67553—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl esterHCID 86624408—

Reaction Conditions

Temperature70 °C

Reaction Steps

3-Bromomethylbenzoic acid methyl ester (0.77 g), K2CO3 (1.0 g) and a catalytic amount of n-Bu4NI were added to a solution of 5-bromo-3-ethoxy-4-hydroxybenzaldehyde (0.75 g) in 10 mL DMF and the reaction mixture was stirred at 70° C. for 1 h. A solution of 3% citric acid in water was added and the reaction mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, dried over MgSO4 and concentrated. The title compound was obtained after flash column chromatography (silica gel, heptane/ethyl acetate (1/4, v/v), Rf=0.25).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07994189B2
Source datasetuspto-grants-2011_08
ORD IDord-5ad6e7ba929e47ae901675011fb6676b
Source noteuspto-grants-2011_08