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

HRID 1257194Notes

Reaction equation

HRID 1257194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>FC(F)(F)C1C=CC=CC=1>[Br:19][CH2:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-

Product 1

HCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzeneYield 84.6%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

A mixture of 2-fluoro-5-nitrotoluene (0.750 g, 4.83 mmol), NBS (1.549 g, 8.70 mmol) and AIBN (0.159 g, 0.967 mmol) in trifluorotoluene (15 ml) was heated to reflux overnight. The mixture was cooled RT, the solids removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford ˜80% pure 2-(bromomethyl)-1-fluoro-4-nitrobenzene (956 mg, 63% yield).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe solids removed via filtration
  4. concentrationthe filtrate concentrated to dryness
  5. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-a13b62fed5644a9aaac8373afd6345ab
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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