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

HRID 1947859Notes

Reaction equation

HRID 1947859 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-d77c0e73819e4510b2217ea540e27b4a
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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