Azobisisobutyronitrile → 1-(Bromomethyl)-4-fluoro-2-iodobenzene

HRID 1711084Notes

Reaction equation

HRID 1711084 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[C:24]([I:29])[CH:23]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:28][C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][C:24]=1[I:29]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 832204-Fluoro-2-iodotoluene

Product 1

HCID 128060541-(Bromomethyl)-4-fluoro-2-iodobenzeneYield 58%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (0.61 g, 3.4 mmol) and VAZO (0.10 g, 0.41 mmol) were added to a solution of 4-fluoro-2-iodotoluene (0.75 g, 3.2 mmol) in carbon tetrachloride (45 mL). The resulting suspension was stirred and heated under reflux for 18 hours. It was then cooled and filtered, the solid was rinsed with carbon tetrachloride (5 mL), and the combined filtrates were concentrated under reduced pressure. The residue was purified by flash column chromatography (eluting with hexanes) to provide 322 (0.58 g, 58% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.51 (dd, J=8.0, 2.5 Hz, 1H); 7.38 (dd, J=8.4, 5.7 Hz, 1H); 7.00 (dt, J=8.2, 2.7 Hz, 1H); 4.54 (s, 2H).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. washthe solid was rinsed with carbon tetrachloride (5 mL)
  6. concentrationthe combined filtrates were concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography (eluting with hexanes)

Sources & evidence

ORD record
ord-2330a2641b644ba894609481f9315db2
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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