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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 496642Generated: October 30, 2026

Tributylamine → HCID 22321883, compound

https://huagongshe.com/reaction/496642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylamineHCID 7622—
Reactant4-FluorostyreneHCID 67883—
ReactantMethyl 2-Bromo-5-nitrobenzoateHCID 245494—
ReactantSodium BicarbonateHCID 516892—
CatalystDichlorobis(triphenylphosphine)palladiumHCID 6102075—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductHCID 22321883HCID 22321883—

Reaction Steps

A mixture of methyl 2-bromo-5-nitrobenzoate (5 g), 4-fluorostyrene (3.5 g), tributylamine (0.39 g), bis-(triphenylphosphine)-palladium(II)chloride (0.3 g), sodium bicarbonate (2.65 g) and water (30 ml) was stirred and heated at reflux under an argon atmosphere for 1.5 hours. The reaction was then cooled, suspended in dichloromethane (200 ml) and passed through a pad of silica (chromatography grade) eluting with more dichloromethane The dichloromethane was then evaporated away and the residue treated with iso-hexane (200 ml) to give methyl 2-[2-(4-fluorophenyl)ethynyl]-5-nitrobenzoate (compound 74) as a yellow precipitate which was filtered and dried, (5.05 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06946468B1
Source datasetuspto-grants-2005_09
ORD IDord-a613a5e0c3af4116812696498bbd08b5
Source noteuspto-grants-2005_09