Azobisisobutyronitrile → 2-[4-(Bromomethyl)-3-fluorophenyl]-1H-isoindole-1,3(2H)-dione

HRID 1861938Notes

Reaction equation

HRID 1861938 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 6833332-(3-fluoro-4-methylphenyl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 186217392-[4-(Bromomethyl)-3-fluorophenyl]-1H-isoindole-1,3(2H)-dioneYield 46.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the compound (1.0 g) obtained in Example 248, N-bromosuccinimide (698 mg), α,α′-azobis(isobutyronitrile) (catalytic amount) and carbon tetrachloride (20 ml) was heated under reflux for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=8:2) to give 605 mg of the titled compound (yield, 46%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-a27b827d9e374742a1868381b22c1f70
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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