Benzoyl Peroxide → 5-(Bromomethyl)-2-(trifluoromethyl)pyridine

HRID 622710Notes

Reaction equation

HRID 622710 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:10][C:8]([F:11])([F:9])[C:5]1[CH:4]=[CH:3][C:2]([CH2:1][Br:12])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 144227915-Methyl-2-(trifluoromethyl)pyridine

Product 1

HCID 144051255-(Bromomethyl)-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methyl-2-trifluoromethylpyridine (see J. Org. Chem., vol. 29, pages 569-571) (8.1 g) was dissolved in 50 ml of carbon tetrachloride, and N-bromosuccinimide (8.9 g) and a catalytic amount of benzoyl peroxide were added. The mixture was refluxed for 7 hours with stirring. The reaction mixture was cooled, and insoluble materials were collected by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 2-trifluoromethyl-5-pyridylmethyl bromide (also known as 5-bromomethyl-2-trifluoromethylpyridine) (7.3 g).

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationinsoluble materials were collected by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40f2620b54a34a33819f77c0004ce333
Source dataset
uspto-grants-1988_09
Patent number
US04772620

Reaction notes

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