Azobisisobutyronitrile → 7-Bromomethyl-4-(3-furyl)coumarin

HRID 260441Notes

Reaction equation

HRID 260441 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:15]3[C:10](=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=3)[O:9][C:8](=[O:17])[CH:7]=2)=[CH:2]1.C1C(=O)N([Br:25])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:25][CH2:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)=[CH:7][C:8](=[O:17])[O:9]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 233701904-(3-Furyl)-7-methylcoumarin

Product 1

HCID 157805647-Bromomethyl-4-(3-furyl)coumarinYield 42.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-(furan-3-yl)-7-methylcoumarin (1.2 g, 5.3 mmol) in CCl4 (40 mL) was added NBS (1 g, 5.8 mmol) followed by AIBN (87 mg, 0.53 mmol). The resulting mixture was refluxed for 4 h, then cooled to r.t. filtered and evaporated. Purification by chromatrography on silica gel gave 682 mg (42%) of the title compound.

Workup

  1. temperatureThe resulting mixture was refluxed for 4 h
  2. filtrationfiltered
  3. customevaporated
  4. customPurification by chromatrography on silica gel

Sources & evidence

ORD record
ord-14da0efd0a7047c2a16605ed15a28977
Source dataset
uspto-grants-1996_06
Patent number
US05527827

Reaction notes

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