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

HRID 2121314Notes

Reaction equation

HRID 2121314 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>[Fe].C(Cl)(Cl)Cl>[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
90 °C

Procedure

2-Phenylpyridine 3 g(19.3 mmol) and iron powder 40 mg(0.716 mmol) were mixed and stirred. Bromine 4.0 g (25 mmol) was added dropwise with stirring at 0° C., avoiding the rising temperature. Then the mixture was heated up to 90° C. and keep the temperature for ten hours with stirring. After the completion of the reaction, this reaction mixture was dissolved into chloroform solution and washed with 5% aqueous sodium thiosulfate solution. After dried by sodium sulufate, the organic solution was concentrated by an evaporator. The residue obtainedwas purifiedbyuse of silica gel column chromatography. 1.6 g (6.83 mmol) of 2-(bromophenyl)pyridine was obtained and the yield was 35.4%. Analysis: M+=234.0 By FD-MS.

Workup

  1. stirringwith stirring at 0° C.
  2. customfor ten hours
  3. stirringwith stirring
  4. customAfter the completion of the reaction
  5. washwashed with 5% aqueous sodium thiosulfate solution
  6. dry with materialAfter dried by sodium sulufate
  7. concentrationthe organic solution was concentrated by an evaporator

Sources & evidence

ORD record
ord-2e2663cb402a498e9c71ffccaeb94064
Source dataset
uspto-grants-2004_02
Patent number
US06696180B2

Reaction notes

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