Dimethylformamide → HCID 18399427, compound

HRID 1019408Notes

Reaction equation

HRID 1019408 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([Br:25])[C:22]=1[O:23][CH3:24])[C:5]([C:7]1[CH:15]=[C:14]([O:16][CH3:17])C(OC)=C[C:8]=1C(O)=O)=O.[C:26](=[O:29])([O-:28])[O-].[K+].[K+].Br[CH:33](C(OC)=O)[C:34]([O:36]C)=[O:35].[C:42]([O:45][CH2:46][CH3:47])(=O)[CH3:43].[CH3:48]N(C)C=O>O>[Br:25][C:21]1[CH:20]=[C:4]([C:5]2[C:7]3[C:8](=[CH:43][C:42]([O:45][CH2:46][CH3:47])=[C:14]([O:16][CH2:17][CH3:48])[CH:15]=3)[C:26](=[O:29])[O:28][C:33]=2[C:34]([OH:36])=[O:35])[CH:3]=[C:2]([Br:1])[C:22]=1[O:23][CH3:24]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 70087Dimethyl bromomalonateHCID 18398791HCID 18398791, compound

Product 1

HCID 18399427HCID 18399427, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(3,5-dibromo-4-methoxybenzoyl)-4,5-dimethoxy-benzoic acid (6.30 g) in dimethylformamide (50 ml) are added potassium carbonate (4.04 g) and dimethyl bromomalonate (3.43 g), and the mixture is stirred at room temperature overnight. To the reaction mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. To the residue are added dioxane (30 ml) and conc. hydrochloric acid (30 ml), and the mixture is heated under reflux for five hours. The reaction mixture is cooled, and thereto are added ethyl acetate and water. The ethyl acetate layer is separated, and washed. The remaining aqueous layer is acidified with 10% hydrochloric acid, and then extracted with ethyl acetate. The extract is washed, and dried. The extracts are combined, and concentrated under reduced pressure. The residue is crystallized from ether to give 4(3,5-dibromo-4-methoxyphenyl)-6,7-diethoxy-isocoumarin-3-carboxylic acid (1.32 g) as listed in Table 58.

Workup

  1. customThe ethyl acetate layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue are added dioxane (30 ml) and conc. hydrochloric acid (30 ml)
  6. temperaturethe mixture is heated
  7. temperatureunder reflux for five hours
  8. temperatureThe reaction mixture is cooled
  9. additionare added ethyl acetate and water
  10. customThe ethyl acetate layer is separated
  11. washwashed
  12. extractionextracted with ethyl acetate
  13. washThe extract is washed
  14. customdried
  15. concentrationconcentrated under reduced pressure
  16. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-7a2f8193e5b445b08ad62d88a7720322
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

Loading…