Benzoyl Peroxide → 1-(Bromomethyl)-2-chloro-4-fluorobenzene

HRID 1987454Notes

Reaction equation

HRID 1987454 reaction equation
[Cl: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:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 967472-Chloro-4-fluorotoluene

Product 1

HCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 77.6 g (0.54 mol) of 2-chloro-4-fluorotoluene, 95.6 g (0.54 mol) of N-bromosuccinimide, 1 g of benzoyl peroxide, and 1000 ml of carbon tetrachloride were refluxed for 3 h. The resulting mixture was cooled to room temperature and then filtered through a glass frit (G3). The precipitate was additionally washed with 3×100 ml of carbon tetrachloride. The combined filtrate was evaporated to dryness. Fractional distillation of the residue gave pure title product, bp 97-99° C./10 mm Hg. Yield 106 g (88%).

Workup

  1. temperaturewere refluxed for 3 h
  2. filtrationfiltered through a glass frit (G3)
  3. washThe precipitate was additionally washed with 3×100 ml of carbon tetrachloride
  4. customThe combined filtrate was evaporated to dryness
  5. distillationFractional distillation of the residue

Sources & evidence

ORD record
ord-15325dd3f6aa4f96a66387ab2abbce35
Source dataset
uspto-grants-2009_06
Patent number
US07550544B2

Reaction notes

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