Benzoyl Peroxide → 2-(Bromomethyl)-5-phenylpyridine

HRID 1084427Notes

Reaction equation

HRID 1084427 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 767442-Methyl-5-phenylpyridine

Product 1

HCID 151713012-(Bromomethyl)-5-phenylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methyl-5-phenylpyridine (step 1) (169 mg) and N-bromosuccinimide (177 mg) in CCl4 (3 cc) was added benzoyl peroxide (25 mg) and the mixture irradiated with visible light for 5 hours under reflux. After removal of the solvent the residue was purified by chromatography to afford the title compound.

Workup

  1. customthe mixture irradiated with visible light for 5 hours
  2. temperatureunder reflux
  3. customAfter removal of the solvent the residue
  4. customwas purified by chromatography

Sources & evidence

ORD record
ord-a97a4472755f4342acbde25e2376e4dd
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Reaction notes

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