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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1916735Generated: October 27, 2026

Sodium Carbonate → 5-Bromo-2-(4-chlorophenyl)pyridine

https://huagongshe.com/reaction/1916735

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant5-Bromo-2-iodopyridineHCID 593690—
Reactantp-Chlorophenylboric acidHCID 17810664—
SolventMethanolHCID 887—
Solvent1,4-DioxaneHCID 31275—
Product5-Bromo-2-(4-chlorophenyl)pyridineHCID 13128383—

Reaction Conditions

Temperature110 °C

Reaction Steps

Under an N2 atmosphere 11 mL 2 M Na2CO3 solution and 240 mg (0.21 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 3.00 g (10.6 mmol) 5-bromo-2-iodo-pyridine and 3.37 g (21.1 mmol) 4-chlorophenyl-boric acid in 60 mL 1,4-dioxane and 15 mL MeOH and the reaction mixture is heated to 110° C. for 3 h. The mixture is evaporated down i. vac., the residue is combined with 50 mL water, 10 mL 3% NH3 solution and 150 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618132B2
Source datasetuspto-grants-2013_12
ORD IDord-f1459f5f2dd94fb7962303a1d93132c3
Source noteuspto-grants-2013_12