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

HRID 1987455Notes

Reaction equation

HRID 1987455 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[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]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][Br:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 967432-Bromo-5-fluorotoluene

Product 1

HCID 5179721-Bromo-2-(bromomethyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 18.9 g (100 mmol) of 2-bromo-5-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 resulting 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 19.0 g (71%).

Workup

  1. temperaturewere refluxed for 2 h
  2. filtrationThe resulting 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-c3ba283a3fba431f8946ce08566fbc45
Source dataset
uspto-grants-2009_06
Patent number
US07550544B2

Reaction notes

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