Azobisisobutyronitrile → 3-(Bromomethyl)-6-(trifluoromethyl)pyridazine

HRID 420707Notes

Reaction equation

HRID 420707 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[N:3]=[N:4][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 206919503-Methyl-6-(trifluoromethyl)pyridazine

Product 1

HCID 585794043-(Bromomethyl)-6-(trifluoromethyl)pyridazineYield 14%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methyl-6-(trifluoromethyl)pyridazine (70 mg), N-bromosuccinimide (84 mg), azobisisobutyronitrile (14.1 mg), and CCl4 (3 ml) was heated under reflux for 2 days. The solvent was evaporated to dryness under vacuum. The residue obtained was purified by chromatography column on silica gel (AIT, Flashsmart BP-SUP, 20-40 μm) using a mixture of EtOAc/hexane as eluent to give 14 mg (14%) of the title compound along with 15.3 mg (11%) of the dibrominated derivative.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. customThe solvent was evaporated to dryness under vacuum
  4. customThe residue obtained
  5. customwas purified by chromatography column on silica gel (AIT, Flashsmart BP-SUP, 20-40 μm)
  6. additiona mixture of EtOAc/hexane as eluent

Sources & evidence

ORD record
ord-88f16330730444bf947360ffe88e8a03
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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