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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 629349Generated: October 26, 2026

Sodium Carbonate → HCID 90423168, compound

https://huagongshe.com/reaction/629349

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantCyclopropylboronic acidHCID 2760897—
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
ReactantMethyl 4-bromo-2-hydroxybenzoateHCID 13983552—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
ProductHCID 90423168HCID 90423168725.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of methyl 4-bromo-2-hydroxybenzoate (3.00 g) in toluene (30.0 mL) were added tris(dibenzylideneacetone)dipalladium(0) (0.60 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.53 g), cyclopropylboronic acid (2.79 g) and sodium carbonate (3.44 g), and the mixture was stirred overnight at 100° C. under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.80 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09315458B2
Source datasetuspto-grants-2016_04
ORD IDord-a450396b452e46258c5dd273c89950af
Source noteuspto-grants-2016_04