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

HRID 1093917Notes

Reaction equation

HRID 1093917 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

3-Bromo-2-chloro-6-fluoro-toluene (8.0 g), N-bromosuccinimide (NBS) (6.42 g) and a catalytic amount of benzoyl peroxide in carbon tetrachloride (40 ml) were 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 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-fluorobenzene as an off-white solid (10.7 g).

Workup

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

Sources & evidence

ORD record
ord-bb0dccba06ac4f86b58be026ade3954f
Source dataset
uspto-grants-2012_03
Patent number
US08133847B2

Reaction notes

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