Azobisisobutyronitrile → 1-(Bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzene

HRID 1610752Notes

Reaction equation

HRID 1610752 reaction equation
[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:28]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:28][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C:2]([F:15])([F:1])[C:11]([F:13])([F:12])[F:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 127568504-(2,2,3,3,3-Pentafluoropropyl)toluene

Product 1

HCID 222623121-(Bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzeneYield 31%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-(2,2,3,3,3-pentafluoropropyl)toluene (9.97 g, 39.4 mmol) in carbon tetrachloride (300 ml) were added 2,2′-azobisisobutyronitrile (0.33 g, 197 mmol) and N-bromosuccinimide (8.50 g, 47.3 mmol) and the mixture was heated under reflux overnight. After cooling to room temperature, insoluble material was filtered off, and the filtrated was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 50:1, 20:1) to give 1-(bromomethyl)-4-(2,2,3,3,3-pentafluoropropyl)benzene (3.66 g, 31% (yield by two steps)) as colorless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationinsoluble material was filtered off
  4. concentrationthe filtrated was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:0, 50:1, 20:1)

Sources & evidence

ORD record
ord-175b33ddc9c94cd897e92ccdd0b357f4
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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