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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1359289Generated: October 31, 2026

O-Xylene → 4-Benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)pyridine

https://huagongshe.com/reaction/1359289

Reaction equation

Participants

RoleNameHCIDCharge
ReactantO-XyleneHCID 7237—
ReactantStannane, 1,3-benzodioxol-5-yltributyl-HCID 11112375—
Reactant4-Benzyl-5-bromo-2-pyridyl trifluoromethanesulfonateHCID 18182181—
CatalystTetrabutylammonium ChlorideHCID 70681—
SolventEthyl acetate hexaneHCID 21226206—
Product4-Benzyl-5-bromo-2-(3,4-methylenedioxyphenyl)pyridineHCID 1818224938.1%

Reaction Steps

A mixture of 400 mg of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate, 410 mg of (3,4-methylenedioxyphenyl)tributyltin, 300 mg of tetrabutylammonium chloride, 20 mg of tetrakis(triphenylphsphine)palladium(0) and 2 ml of xylene was stirred under heating for 3 hours in an oil bath kept at 140° C. in a nitrogen atmosphere. The reaction solution was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 140 mg of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06599917B1
Source datasetuspto-grants-2003_07
ORD IDord-b049a19658c6490ab28dc1781d34c672
Source noteuspto-grants-2003_07