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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1907695Generated: November 2, 2026

Hexane → 5-Bromo-2-(3,4-dimethoxyphenyl)pyridine

https://huagongshe.com/reaction/1907695

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHexaneHCID 8058—
ReactantSodium CarbonateHCID 10340—
Reactant2,5-DibromopyridineHCID 69353—
Reactant3,4-Dimethoxyphenylboronic acidHCID 2734702—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
Product5-Bromo-2-(3,4-dimethoxyphenyl)pyridineHCID 1397974176%

Reaction Conditions

Temperature75 °C

Reaction Steps

To a degassed solution of 2,5-dibromopyridine 35 (0.50 g, 2.11 mmol), 3,4-dimethoxyphenylboronic acid 36 (0.50 g, 2.74 mmol) and sodium carbonate (0.67 g, 6.3 mmol) in ethyleneglycol dimethylether (7 mL) and H2O (2 mL) was added tetrakis(triphenylphosphine)-palladium(0) (0.16 g, 0.14 mmol) and the solution was stirred at 75° C. for 18 h. The reaction mixture was filtered, concentrated, diluted with AcOEt, washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography of the residue (eluent: 3:1 hexane:AcOEt) provided title compound 37 (0.47 g, 76% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08598168B2
Source datasetuspto-grants-2013_12
ORD IDord-b8b1e079f9094a7d8e7d213873616319
Source noteuspto-grants-2013_12