Benzoyl Peroxide → 1-Bromo-3-(bromomethyl)-2-chloro-4-fluorobenzene

HRID 1512069Notes

Reaction equation

HRID 1512069 reaction equation
[Br:1][C:2]1[C:3]([Cl:10])=[C:4]([CH3:9])[C:5]([F:8])=[CH:6][CH:7]=1.[Br:11]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])=[C:4]([CH2:9][Br:11])[C:3]=1[Cl:10]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27362273-Bromo-2-chloro-6-fluorotoluene

Product 1

HCID 579988441-Bromo-3-(bromomethyl)-2-chloro-4-fluorobenzeneYield 98.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-bromo-2-chloro-6-fluoro-toluene (8.0 g), N-bromosuccinimide (“NBS”) (6.42 g) and benzoyl peroxide (catalytic amount) in carbon tetrachloride (40 ml) was heated to reflux. A 500 watt tungsten halogen lamp was used to initiate the reaction. The reaction mixture was heated to reflux and irradiated for 30 minutes. The reaction mixture was allowed to cool to ambient temperature and then filtered. The filtrate was concentrated to give a colourless oil which solidified on standing to give 1-bromo-3-bromomethyl-2-chloro-4-fluoro-benzene as an off-white solid (10.7 g). 1H-NMR (400 MHz, CDCl3): 4.64 (d, 2H), 6.94 (t, 1H), 7.58 (dd, 1H) ppm.

Workup

  1. temperaturewas heated to reflux
  2. customthe reaction
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. customirradiated for 30 minutes
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto give a colourless oil which

Sources & evidence

ORD record
ord-51ba7c88e265423d92f15ee6e728fa46
Source dataset
uspto-grants-2012_07
Patent number
US08217055B2

Reaction notes

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