Phenol → 2-Bromo-6-phenoxypyridine

HRID 1183411Notes

Reaction equation

HRID 1183411 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CC(C)([O-])C.[K+]>CS(C)=O>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 122742,6-DibromopyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 8245892-Bromo-6-phenoxypyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

2,6-Dibromo-pyridine (2 g, 8.44 mmol) and phenol (0.794 g, 8.44 mmol) were dissolved in DMSO (20 mL) and potassium tert-butoxide (0.947 g, 8.44 mmol) was added. The reaction was heated to 160° C. overnight then allowed to cool to room temperature. The reaction was submitted to aqueous workup and silica gel chromatography to afford the title compound.

Workup

  1. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-bfe40919a67f45a39a9a6a44f42e9d2d
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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