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Azobisisobutyronitrile → 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

HRID 635904
Notes
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Reaction equation

HRID 635904 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[C:21]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[O:29][C:28]([CH3:34])([CH3:33])[CH2:27][CH2:26]2)#[N:22]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH:26]1[C:25]2[C:30](=[CH:31][CH:32]=[C:23]([C:21]#[N:22])[CH:24]=2)[O:29][C:28]([CH3:34])([CH3:33])[CH2:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 109212656-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Product 1

HCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

11 mmol of N-bromosuccinimide and 0.22 g of azobisisobutyronitrile (Aldrich) are added to a solution of 10 mmol of 6-cyano-2,2-dimethyl-chroman in 30 ml of carbon tetrachloride and the suspension thus obtained is heated to boiling under a reflux condenser for 3 hours. Insoluble succinimide is then filtered off, the solvent is distilled off and the residue is crystallized under a mixture of n-hexane and diisopropyl ether.

Workup

  1. customthe suspension thus obtained
  2. temperatureis heated
  3. filtrationInsoluble succinimide is then filtered off
  4. distillationthe solvent is distilled off
  5. customthe residue is crystallized under a mixture of n-hexane and diisopropyl ether

Sources & evidence

ORD record
ord-189a043104d84f949f287bc8269b7434
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06191164B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes