Azobisisobutyronitrile → 1-(Bromomethyl)-3-fluoro-5-nitrobenzene

HRID 1430545Notes

Reaction equation

HRID 1430545 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.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:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 150652441-Fluoro-3-methyl-5-nitrobenzene

Product 1

HCID 647705451-(Bromomethyl)-3-fluoro-5-nitrobenzeneYield 63%

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 3-fluoro-5-nitrotoluene (1.0 g, 6.45 mmol) in trifluorotoluene (15 ml) was treated with NBS (1.721 g, 9.67 mmol) and AIBN (0.212 g, 1.289 mmol) and heated at 105° C. overnight. The mixture was cooled to RT, the solids removed via filtration and the filtrate concentrated to dryness to afford 1-(bromomethyl)-3-fluoro-5-nitrobenzene (95 mg, 63% yield).

Workup

  1. temperatureThe mixture was cooled to RT
  2. customthe solids removed via filtration
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-7571780bdebc4b4ab84ba4cdc975f06e
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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