Azobisisobutyronitrile → 2-(Bromomethyl)-4-nitrobenzonitrile

HRID 1912643Notes

Reaction equation

HRID 1912643 reaction equation
[CH3:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 43463672-Methyl-4-nitrobenzonitrile

Product 1

HCID 598380122-(Bromomethyl)-4-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A degassed solution of 2-methyl-4-nitrobenzonitrile (10 g, 61.7 mmol), N-bromosuccinimide (13.2 g (74.17 mmol, 1.2 eq.) and azobisisobutyronitrile (AlBN) (2.0 g, 12.18 mmol, 0.2 eq) in 300 ml CCl4 was heated at reflux for 3 days. After solvent was evaporated the residue was taken in ethyl acetate and washed 2× with aq. NaHCO3, aq. Na2S2O3, brine, dried over MgSO4, filtered, concentrated and purified chromatography using 15% ethyl acetate in hexane to provide 11.7 g of 2-bromomethyl-4-nitrobenzonitrile.

Workup

  1. temperatureat reflux for 3 days
  2. customAfter solvent was evaporated the residue
  3. washwashed 2× with aq. NaHCO3, aq. Na2S2O3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified chromatography

Sources & evidence

ORD record
ord-918b183bc3eb4ad1823601baf391f9d4
Source dataset
uspto-grants-2013_12
Patent number
US08609676B2

Reaction notes

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