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

HRID 1674463Notes

Reaction equation

HRID 1674463 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-phenyl pyridine and 40 mg (0.716 mmol) of iron powder were mixed and stirred. It was cooled to 0° C. and 4.0 g (25 mmol) of bromine was added dropwise with stirring, and watching heat generation, and it was raised to 90° C., and stirred for 10 hours. After the reaction, this reaction mixture was dissolved in chloroform to produce a solution, which was washed with 5% sodium thiosulfate aqueous solution. The chloroform solution was dried with sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography, and the desired 2-(bromophenyl)pyridine was obtained.

Workup

  1. stirringwith stirring
  2. temperaturewatching heat generation, and it
  3. temperaturewas raised to 90° C.
  4. stirringstirred for 10 hours
  5. customAfter the reaction
  6. customto produce a solution, which
  7. washwas washed with 5% sodium thiosulfate aqueous solution
  8. dry with materialThe chloroform solution was dried with sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8958d83f4bb5430fae065f23e858a49b
Source dataset
uspto-grants-2011_08
Patent number
US08003226B2

Reaction notes

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