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

HRID 2279774Notes

Reaction equation

HRID 2279774 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C1C(=O)N([Br:19])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>FC(F)(F)C1C=CC=CC=1>[Br:19][CH2:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1234783-Chloro-4-nitrotoluene

Product 1

HCID 671933714-(Bromomethyl)-2-chloro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

A solution of 3-chloro-4-nitrotoluene (2.0 g, 12 mmol), NBS (2.62 g, 14.6 mmol) and 2,2′-azo-bis-isobutyronitrile (0.195 g, 1.16 mmol) in α,α,α-trifluorotoluene (200 mL) was heated at 80° C. under an atmosphere of nitrogen for 3 h. Solvent was removed in vacuo and the residue was partitioned between EtOAc and water and separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was taken to the next step without purification.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. customseparated
  4. extractionThe aqueous layer was extracted with EtOAc (3×)
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was taken to the next step without purification

Sources & evidence

ORD record
ord-4746a1d597b740af9e5f49161fd261f4
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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