Azobisisobutyronitrile → 1-Bromo-4-(bromomethyl)-2-fluorobenzene

HRID 1424024Notes

Reaction equation

HRID 1424024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][Br:22])=[CH:4][C:3]=1[F:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5732804-Bromo-3-fluorotoluene

Product 1

HCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-bromo-3-fluorotoluene (11.34 g, 60 mmol), azobisisobutyronitrile (0.99 g, 6 mmol), and N-bromosuccinimide (11.75 g, 66 mmol) in carbon tetrachloride (60 ml) was heated to reflux for 3.5 h. The reaction mixture was cooled to room temperature and then filtered through Celite, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:hexane=0:100 to 100:0, gradient) to obtain the title compound (12.8 g, 80%) as a light yellow solid.

Workup

  1. temperatureto reflux for 3.5 h
  2. filtrationfiltered through Celite
  3. distillationthe solvent in the filtrate was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (Isco Combiflash, 40 g, ethyl acetate:hexane=0:100 to 100:0, gradient)

Sources & evidence

ORD record
ord-4d89173051a240788a2fd80cb91253ae
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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