Potassium Carbonate → HCID 18398829, compound

HRID 1019407Notes

Reaction equation

HRID 1019407 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:5]([C:7]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=O.C(=O)([O-])[O-].[K+].[K+].Br[CH:34](C(OCC)=O)[C:35]([O:37]CC)=[O:36]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[C:8](=[CH:12][C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=3)[C:9](=[O:10])[O:11][C:34]=2[C:35]([OH:37])=[O:36])[CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 18399438HCID 18399438, compound

Product 1

HCID 18398829HCID 18398829, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-bromo-4,5-dimethoxybenzoyl)-4,5-dimethoxy-benzoic acid (6 g) in dimethylformamide (110 ml) are added potassium carbonate (4.29 g) and diethyl bromomalonate (3.71 g), and the mixture is stirred at room temperature overnight. The reaction mixture is evaporated to remove dimethylformamide, and to the residue 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 (35 ml) and conc. hydrochloric acid (35 ml), and the mixture is heated under reflux for five hours. The reaction mixture is cooled, and thereto are added chloroform and water. The chloroform layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from ether to give 4-(3-bromo-4,5-dimethoxyphenyl)-6,7-dimethoxyisocoumarin-3-carboxylic acid (2.54 g) as listed in Table 58.

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove dimethylformamide
  3. additionto the residue are added ethyl acetate and water
  4. customThe ethyl acetate layer is separated
  5. washwashed
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. additionTo the residue are added dioxane (35 ml) and conc. hydrochloric acid (35 ml)
  9. temperaturethe mixture is heated
  10. temperatureunder reflux for five hours
  11. temperatureThe reaction mixture is cooled
  12. additionare added chloroform and water
  13. customThe chloroform layer is separated
  14. washwashed
  15. customdried
  16. concentrationconcentrated under reduced pressure
  17. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-1c0777fe408d4bc09d5e2bee618f3908
Source dataset
uspto-grants-2002_11
Patent number
US06486155B1

Reaction notes

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