Ethyl bromoacetate → Ethyl 2-(2-acetyl-4-bromophenoxy)acetate

HRID 361882Notes

Reaction equation

HRID 361882 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[OH:11])(=[O:3])[CH3:2].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Cl)(Cl)Cl>[C:1]([C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[O:11][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 19261366Ethyl 2-(2-acetyl-4-bromophenoxy)acetateYield 90.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

13.31 g of 2-acetyl-4-bromophenol, 11.0 g of ethyl bromoacetate and 9.7 g of anhydrous potassium carbonate were refluxed under heating in 70 ml of acetone for 2 hours. Insoluble materials were removed by filtration, and the resulting filtrate was concentrated and dried. The residue thus obtained was dissolved in chloroform, washed with water, and then dried to remove the solvent. The thus treated residue was washed with a mixed solvent system of ethanol and n-hexane to isolate insoluble crystals by filtration. In this way, 16.82 g of ethyl (2-acetyl-4-bromophenyl)oxyacetate was obtained in the form of colorless plate crystals.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe resulting filtrate was concentrated
  3. customdried
  4. customThe residue thus obtained
  5. washwashed with water
  6. customdried
  7. customto remove the solvent
  8. washThe thus treated residue was washed with a mixed solvent system of ethanol and n-hexane
  9. customto isolate insoluble crystals
  10. filtrationby filtration

Sources & evidence

ORD record
ord-10377a5ac43d4a069c0f8ebe2cdf6ea7
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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