Benzoyl Peroxide → 2-Bromo-1-(bromomethyl)-4-fluorobenzene

HRID 269462Notes

Reaction equation

HRID 269462 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 740162-Bromo-4-fluorotoluene

Product 1

HCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 18.9 g (100 mmol) of 2-bromo-4-fluorotoluene, 17.8 g (100 mmol) of N-bromosuccinimide, 400 mg of benzoyl peroxide, and 200 ml of CCl4 were refluxed for 2 h. The reaction mixture was filtered through a glass frit (G2), and the precipitate was additionally washed with 3×50 ml of CCl4. The combined filtrate was evaporated to dryness. Fractional distillation of the residue (bp 92-96° C./4 mm Hg) gave the title product as colorless oil. Yield 20.4 g (76%).

Workup

  1. temperaturewere refluxed for 2 h
  2. filtrationThe reaction mixture was filtered through a glass frit (G2)
  3. washthe precipitate was additionally washed with 3×50 ml of CCl4
  4. customThe combined filtrate was evaporated to dryness
  5. distillationFractional distillation of the residue (bp 92-96° C./4 mm Hg)

Sources & evidence

ORD record
ord-94c9944c3f9d407eabf4c54ef871c94b
Source dataset
uspto-grants-2008_11
Patent number
US07446216B2

Reaction notes

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