N-bromobutanimide → 4-Bromo-2-(bromomethyl)-1-fluorobenzene

HRID 2296993Notes

Reaction equation

HRID 2296993 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[CH2:8][Br:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1235275-Bromo-2-fluorotoluene

Product 1

HCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzeneYield 101.1%

Reagents, catalysts & solvents 2

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)CatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 9.45 g (50 mmol) of 5-bromo-2-fluorotoluene in 30 ml of carbon tetrachloride were added 9.08 g (50 mmol) of N-bromosuccinimide and 0.26 g (1 mmol) of 1,1′-azobis(cyclohexane-1-carbonitrile) and the mixture was heated under reflux for 5 hours. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was concentrated to obtain 13.54 g of crude 5-bromo-2-fluorobenzylbromide as liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. filtrationthe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1de46c792cf5489bb14841090c5061c9
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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