Benzoyl Peroxide → HCID 18700249, compound

HRID 2352744Notes

Reaction equation

HRID 2352744 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][Br:15])[CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 116728102-(4-Fluorophenyl)-4-methylpyridine

Product 1

HCID 18700249HCID 18700249, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-(p-fluorophenyl)-4-methyl-pyridine (0.5 g, 2.67 mmol), N-bromosuccinimide (0.48 g, 2.69 mmol), and a catalytic amount of benzoylperoxide in CCl4 (50 ml) was stirred at reflux temperature and irradiated by means of an ordinary 250-W UV lamp for 4 hrs. Afterwards, the reaction mixture was cooled and subsequently triturated with Et2O/petroleum benzine. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo to give 2-(p-fluorophenyl)-4-bromomethyl-pyridine (0.63 g, 88%, unstable) as a dark yellow oil.

Workup

  1. temperatureat reflux temperature
  2. customirradiated by means of an ordinary 250-W UV lamp for 4 hrs
  3. temperatureAfterwards, the reaction mixture was cooled
  4. customsubsequently triturated with Et2O/petroleum benzine
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-16a2cde627f94a1c95e63b11caaead5e
Source dataset
uspto-grants-2010_07
Patent number
USRE041425E1

Reaction notes

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