2-Phenylpyridine → 2-(2-Bromophenyl)pyridine

HRID 550326Notes

Reaction equation

HRID 550326 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13]Br>C(Cl)(Cl)Cl.[Fe]>[Br:13][C:6]1[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 2

HCID 138872-PhenylpyridineHCID 24408Bromine

Product 1

HCID 132239292-(2-Bromophenyl)pyridineYield 35.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3 g (19.3 mmol) of 2-phenylpyridine and 40 mg (0.716 mmol) of an iron powder were mixed and stirred. 4.0 g (25 mmol) of bromine was dropped paying attention to heat generation while stirring and cooling the mixture to 0° C., and the mixture was heated up to 90° C. and stirred for 10 hours. After completion of the reaction, this reaction mixture was dissolved in chloroform, and washed with a 5% aqueous sodium thiosulfate solution. The chloroform solution was dried over sodium sulfate, then, concentrated, and the residue was purified by silica gel column chromatography, to obtain the intended 2-(bromophenyl)pyridine.

Workup

  1. temperatureto heat generation
  2. stirringwhile stirring
  3. temperaturethe mixture was heated up to 90° C.
  4. stirringstirred for 10 hours
  5. customAfter completion of the reaction
  6. washwashed with a 5% aqueous sodium thiosulfate solution
  7. dry with materialThe chloroform solution was dried over sodium sulfate
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-66625216ddc04b3990b0170475934285
Source dataset
uspto-grants-2011_05
Patent number
US07947340B2

Reaction notes

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