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

HRID 2379167
Notes
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Reaction equation

HRID 2379167 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 for 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, m.p. 155°-156° C.

Workup

  1. temperatureAfter the mixture was refluxed for 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-9f6891c3e8b8426fb969b87d486762b2
Source dataset
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05360815

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes