2-Chloropyridine → 2,2'-Bipyridine

HRID 1937041Notes

Reaction equation

HRID 1937041 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl-].[Li+].[OH-].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 79772-ChloropyridineHCID 14797Potassium HydroxideHCID 433294Lithium Chloride

Product 1

HCID 14742,2'-BipyridineYield 91%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

50 mmol of 2-chloropyridine are refluxed together with 50 mmol of 2-pyridylboronic acid glycol ester, 25 mmol of lithium chloride, 50 mmol of potassium hydroxide, 1 mmol of tetrabutylammonium chloride and 0.05 mmol of trans-di-μ-acetato-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium (0.2 mol %) in (0.2 mol %) in 150 ml of tetrahydrofuran for 5 hours. Customary aqueous work-up and crystallization of the crude product from ethanol gives 2,2′-bipyridyl as colorless crystals (m.p. 70° C.) in a yield of 91%.

Workup

  1. customCustomary aqueous work-up and crystallization of the crude product from ethanol

Sources & evidence

ORD record
ord-d9232a5e5e7d414fbccd2f0c8825605b
Source dataset
uspto-grants-2002_05
Patent number
US06392047B1

Reaction notes

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