Potassium Carbonate → 2,2'-Oxybis(6-phenylpyridine)

HRID 2117812Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:16]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>>[O:1]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 14798Sodium Hydroxide

HCID 878896-Phenyl-2-pyridone

HCID 5686792-Bromo-6-phenylpyridine

Product 1

HCID 231357882,2'-Oxybis(6-phenylpyridine)Yield 69.1%

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-hydroxy-6-phenylpyridine (1.0 g, 5.8 mmol), 2-bromo-6-phenylpyridine (1.4 g, 5.8 mmol) and potassium carbonate (807 mg, 5.8 mmol) was stirred at 200° C. for 8 hours. After the reaction mixture was cooled, to which was then added an aqueous 1 mol/L sodium hydroxide solution, the mixture was extracted with dichloromethane, the solvent was distilled off, and the residue was purified by silica gel column chromatography, thereby obtaining 1.3 g of 2,2′-oxybis(6-phenylpyridine) as colorless crystal.

Workup

temperatureAfter the reaction mixture was cooled, to which
extractionthe mixture was extracted with dichloromethane
distillationthe solvent was distilled off
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a39f7492da3b4606813ff1046d54954b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442797B2

Reaction notes

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