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

HRID 1168839Notes

Reaction equation

HRID 1168839 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 by a halogen lamp, is heated at reflux for 2 hours. The mixture is then brought to ambient temperature and filtered, and the filtrate is subsequently evaporated, toluene is added, and the suspension obtained is filtered and the filtrate evaporated to yield the expected product.

Workup

  1. customthe reaction mixture, illuminated by a halogen lamp
  2. temperatureis heated
  3. temperatureat reflux for 2 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 evaporated

Sources & evidence

ORD record
ord-c0ab141908034133a826273d051fd0cf
Source dataset
uspto-grants-2003_09
Patent number
US06627650B2

Reaction notes

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