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

HRID 21564Notes

Reaction equation

HRID 21564 reaction equation
[Br:1]N1C(=O)CCC1=O.[O:9]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[O:17][C:16](=[O:25])[CH:15]=2)=[CH:10]1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:24][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([C:11]3[CH:12]=[CH:13][O:9][CH:10]=3)=[CH:15][C:16](=[O:25])[O:17]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

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

Product 1

HCID 157805647-Bromomethyl-4-(3-furyl)coumarinYield 49.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide (0.90 g, 5.06 mmol) was added to a stirred solution of the compound from Step 2 (1.04 g, 4.60 mmol) in CCl4 (150 ml) followed by a catalytic amount of azobis (isobutyronitrile). After the mixture was refluxed 3 h, the precipitated solid was removed by filtration and the solvent was evaporated in vacuo. The residue was stirred for 10 min in 15 ml Et2O, filtered and dried to give 0.69 g of the title compound. mp 155°-156° C.

Workup

  1. temperatureAfter the mixture was refluxed 3 h
  2. customthe precipitated solid was removed by filtration
  3. customthe solvent was evaporated in vacuo
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-b463ae009edb49a39dd9696aea87e002
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Reaction notes

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