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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2390959Generated: October 28, 2026

Hydrochloric Acid → HCID 57615034, compound

https://huagongshe.com/reaction/2390959

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantDiethyl MalonateHCID 7761—
ReactantCesium carbonateHCID 10796—
Reactant5-Bromo-1-benzothiopheneHCID 2776578—
ReactantTri(tert-butyl)phosphine hexaneHCID 86628723—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
ProductHCID 57615034HCID 57615034100.6%

Reaction Steps

To 1,2-dimethoxyethane (10 mL) suspension of 0.02 g of tris(dibenzylideneacetone)dipalladium(0) were added 0.11 g of 10% (w/w) tri(tert-butyl)phosphine/hexane, 1.76 g of cesium carbonate, 0.50 g of 5-bromobenzothiophene and 0.45 g of diethyl malonate, which was then refluxed for 2 hours. To the reaction mixture were added water and ethyl acetate, followed by adjustment to pH2 using 2 mol/L hydrochloric acid. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to provide 0.69 g of diethyl 2-(1-benzothiophen-5-yl)malonate as white solid form.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08273902B2
Source datasetuspto-grants-2012_09
ORD IDord-668dee67ecba4688a987f89563180438
Source noteuspto-grants-2012_09