2-Bromopyridine → 2-(3-Bromophenyl)pyridine

HRID 2117808Notes

Reaction equation

HRID 2117808 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:10]=[C:11](O)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>>[Br:8][C:9]1[CH:14]=[C:13]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 14798Sodium Hydroxide

Product 1

HCID 111155062-(3-Bromophenyl)pyridineYield 78.4%

Conditions

Temperature
200 °C

Procedure

A mixture of 2-bromopyridine (2.5 g, 15.8 mmol), 3-bromophenol (5.5 g, 31.6 mmol) and potassium carbonate (2.2 g, 15.8 mmol) was stirred at 200° C. for 3 hours. After the reaction mixture was allowed to cool, 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 and recrystallization, thereby obtaining 2.9 g of desired compound as white crystal.

Workup

  1. temperatureto cool, to which
  2. extractionthe mixture was extracted with dichloromethane
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography and recrystallization

Sources & evidence

ORD record
ord-5c2b7b5808014c7382626d9debaa5e12
Source dataset
uspto-grants-2008_10
Patent number
US07442797B2

Reaction notes

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