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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2094716Generated: October 30, 2026

Dimethyl malonate → HCID 67239285, compound

https://huagongshe.com/reaction/2094716

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl malonateHCID 7943—
ReactantSodium hydrideHCID 24758—
ReactantMethyl 2-(3-bromophenyl)acetateHCID 11746402—
CatalystTri-tert-butylphosphine tetrafluoroborateHCID 2734635—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTetrahydrofuranHCID 8028—
ProductHCID 67239285HCID 6723928544.3%

Reaction Steps

Tris(dibenzylideneacetone)dipalladium(0) (0.104 g, 0.113 mmol), tri-(tert-butyl)phosphonium tetrafluoroborate (65.8 mg, 0.227 mmol) and sodium hydride (295 mg, 60% dispersion in mineral oil) were charged into a flask under an argon atmosphere. (3-Bromophenyl)acetic acid methyl ester (1.30 g, 5.67 mmol) was dissolved in THF (10 ml) and added to the mixture. Subsequently, dimethyl malonate (0.995 g, 7.37 mmol) was added and the mixture stirred under reflux overnight. The mixture was filtered over a small plug of silica gel, evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 0.704 g of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08445530B2
Source datasetuspto-grants-2013_05
ORD IDord-99637baf7eca4df2852feedea11a709e
Source noteuspto-grants-2013_05