Ethyl bromoacetate → HCID 28829501, compound

HRID 2053174Notes

Reaction equation

HRID 2053174 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:3]=1)[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 121243-Hydroxyacetanilide

Product 1

HCID 28829501HCID 28829501, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(3-hydroxy-phenyl)-acetamide (0.5 g, 3.3 mmol) in acetone (5 ml) was added K2CO3 (0.46 g, 3.3 mmol), ethyl bromoacetate (0.67 g, 4.0 mmol) and 10 4A molecular sieves. The reaction mixture was then heated in the microwave for 1 h at 100° C. (150 W, 200 psi). The reaction mixture was filtered and the acetone layer evaporated in vacuo. This residue was dissolved in EtOAc (10 ml) and washed with 2M KOH (5 ml×2). The organic layer was dried (Na2SO4), filtered and the solvent removed in vacuo to give the title compound as a colourless oil which solidified upon standing.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe acetone layer evaporated in vacuo
  3. dissolutionThis residue was dissolved in EtOAc (10 ml)
  4. washwashed with 2M KOH (5 ml×2)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c29fdb757001476da51d53abe1c85117
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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