Azobisisobutyronitrile → HCID 22648021, compound

HRID 394185Notes

Reaction equation

HRID 394185 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[CH2:12][Br:13]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 70157802,6-DIBROMO-4-NITROTOLUENE

Product 1

HCID 22648021HCID 22648021, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of 2,6-dibromo-4-nitrotoluene (5.00 g, 16.95 mmol) in CCl4 (131 mL) was added N-bromosuccinimide (4.22 g, 23.73 mmol) and dibenzoyl peroxide (411 mg, 1.70 mmol). The mixture was evacuated and flushed with argon three times, then heated using an oil bath. At reflux azo-bis-isobutyronitrile (278 mg, 1.695 mmol) was added. The reaction was stopped after 3.75 h, cooled to rt and filtered washing with CCl4. The filtrate was concentrated under reduced pressure to give a yellow solid, which was purified using flash chromatography on Biotage 40M column, eluting with 90:10 hexanes-CH2Cl2 to yield 1,3-dibromo-2-(bromomethyl)-5-nitrobenzene. 1H NMR (500 MHz, CDCl3): δ 4.8 (s, 2H), 8.4 (s, 2H).

Workup

  1. customThe mixture was evacuated
  2. customflushed with argon three times
  3. temperatureheated
  4. additionwas added
  5. filtrationfiltered
  6. washwashing with CCl4
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give a yellow solid, which
  9. customwas purified
  10. washeluting with 90:10 hexanes-CH2Cl2

Sources & evidence

ORD record
ord-02862b58ce6a4026b70eda7d63d41c3c
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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