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

HRID 1610662Notes

Reaction equation

HRID 1610662 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

A solution of 3-(1,1,2,2-tetrafluoroethoxy)toluene (12.5 g, 60.0 mmol), N-bromosuccinimide (10.7 g, 60.0 mmol) and 2,2′-azobis(isobutyronitrile) (30 mg) in carbon tetrachloride (30 ml) was heated under reflux for 0.5 hr. After cooling the reaction solution to room temperature, 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. temperatureunder reflux for 0.5 hr
  2. customwhite precipitate was removed by filtration
  3. washthe-precipitate was washed with diethyl ether
  4. customThe solvent of the recovered filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5ab3f944383447debbf16bf120d960d1
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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