Azobisisobutyronitrile → 1-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

HRID 1610682Notes

Reaction equation

HRID 1610682 reaction equation
[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[Br:15]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[CH2:13][Br:15])[CH:3]([F:4])[F:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 74438Benzene, 1-methyl-3-(1,1,2,2-tetrafluoroethoxy)-

Product 1

HCID 114603781-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-(1,1,2,2-Tetrafluoroethoxy)toluene (48.4 g, 233 mmol), N-bromosuccinimide (41.4 g, 233 mmol) and 2,2′-azobis(isobutyronitrile) (0.1 g) were heated under reflux in carbon tetrachloride (100 ml) for 0.5 hr. After cooling the reaction solution to room temperature, the white precipitate was removed by filtration, and the precipitate was washed with diethyl ether. The solvent of the recovered filtrate was evaporated under reduced pressure to give a crude product of 3-(1,1,2,2-tetrafluoroethoxy)benzyl bromide as a pale-yellow liquid.

Workup

  1. customthe white precipitate was removed by filtration
  2. washthe precipitate was washed with diethyl ether
  3. customThe solvent of the recovered filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a6b48f3294149cebdfc0757ce0dc882
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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