N-bromobutanimide → 3-Bromo-5,6-dimethoxy-phthalide

HRID 991880

Reaction equation

HRID 991880 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[C:16](=[O:17])[O:15][CH2:14]2>ClCCl>[Br:1][CH:14]1[C:13]2[C:18](=[CH:19][C:20]([O:21][CH3:22])=[C:11]([O:10][CH3:9])[CH:12]=2)[C:16](=[O:17])[O:15]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2304605,6-Dimethoxy-3H-isobenzofuran-1-one

Product 1

HCID 111965723-Bromo-5,6-dimethoxy-phthalide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12 mmol of N-bromosuccinimide are added to 10 mmol of 5,6-dimethoxyphthalide dissolved in dichloromethane and then the reaction mixture, illuminated with a halogen lamp, is heated at reflux for 5 hours. The mixture is then brought to ambient temperature and filtered, and the filtrate is subsequently evaporated, toluene is added, the suspension obtained is filtered and the filtrate is evaporated. The residue obtained is filtered through silica to yield the expected product.

Workup

  1. customthe reaction mixture, illuminated with a halogen lamp
  2. temperatureis heated
  3. temperatureat reflux for 5 hours
  4. customis then brought to ambient temperature
  5. filtrationfiltered
  6. customthe filtrate is subsequently evaporated
  7. additiontoluene is added
  8. customthe suspension obtained
  9. filtrationis filtered
  10. customthe filtrate is evaporated
  11. customThe residue obtained
  12. filtrationis filtered through silica

Sources & evidence

ORD record
ord-92ff867ea2ef498bbbe1006bdae4a4e0
Source dataset
uspto-grants-2002_10
Patent number
US06465660B1

Linked notes

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