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

HRID 1760755Notes

Reaction equation

HRID 1760755 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-dimethoxy-phthalide dissolved in dichloromethane, and then the reaction mixture, lit by a halogen lamp, is refluxed for 5 hours. The mixture is then returned to room temperature and filtered, and the filtrate is evaporated, toluene is added, the resulting suspension is filtered and the filtrate is evaporated. The resulting residue is filtered over silica to yield the expected product.

Workup

  1. temperaturethe reaction mixture, lit by a halogen lamp, is refluxed for 5 hours
  2. customis then returned to room temperature
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. additiontoluene is added
  6. filtrationthe resulting suspension is filtered
  7. customthe filtrate is evaporated
  8. filtrationThe resulting residue is filtered over silica

Sources & evidence

ORD record
ord-bafe7cf7d1b94a3cb869a3bd0a91b066
Source dataset
uspto-grants-2005_01
Patent number
US06844445B2

Reaction notes

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