Ethyl bromoacetate → ethyl {[5-chloro-3-(2-methylphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetate

HRID 1905083Notes

Reaction equation

HRID 1905083 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([OH:20])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CC(C)=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:20][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14254481HCID 14254481, compound

Product 1

HCID 14254503ethyl {[5-chloro-3-(2-methylphenyl)-4-oxo-4H-1-benzopyran-7-yl]oxy}acetateYield 89.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 1 l of acetone was suspended 114 g of 5-chloro-7-hydroxy-3-(2-methylphenyl)-4-oxo-4H-1-benzopyran, and 60.4 g of anhydrous potassium carbonate and 73.0 g of ethyl bromoacetate were added thereto, followed by refluxing for 1.5 hours. After cooling, the insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. Recrystallization of the residue from ethanol gave 132 g of the entitled compound having a melting point of 122° to 123° C.

Workup

  1. additionwere added
  2. temperatureby refluxing for 1.5 hours
  3. temperatureAfter cooling
  4. customthe insoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-15ba9e5435da4645b9b14cb78f297770
Source dataset
uspto-grants-1989_06
Patent number
US04841076

Reaction notes

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