Ethyl bromoacetate → ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetate

HRID 650817Notes

Reaction equation

HRID 650817 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]([NH:17][CH3:18])=[O:16].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O.[I-].[K+]>[CH3:18][NH:17][C:15]([CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 217123112-(2-hydroxyphenyl)-N-methylacetamide

Product 1

HCID 10848339ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetateYield 103%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

Potassium carbonate (2.81 g, 20.34 mmol) was given to a solution of 2-(2-hydroxyphenyl)-N-methylacetamide (3.36 g, 20.34 mmol) in acetone (150 ml). Ethyl bromoacetate (2.13 ml, 19.32 mmol) and potassium iodide (166 mg, 1.02 mmol) were added successively. The reaction mixture was heated to reflux for 6 h. It was left at room temperature for 16 h. The solid was filtered off. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using ethyl acetate/dichloromethane (1:1) as eluent, to give 5.00 g of ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe solid was filtered off
  4. customThe solvent was removed in vacuo
  5. customThe crude product was purified by flash chromatography on silica (80 g)

Sources & evidence

ORD record
ord-88a7f8985efd4fd993c0a1b881b79067
Source dataset
uspto-grants-2001_08
Patent number
US06274584B1

Reaction notes

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