Ethyl bromoacetate → Ethyl 2-(4-methoxyphenoxy)acetate

HRID 922318Notes

Reaction equation

HRID 922318 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 90154-MethoxyphenolHCID 11430Potassium Carbonate

Product 1

HCID 240125Ethyl 2-(4-methoxyphenoxy)acetateYield 118.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL RB flask fitted with magnetic stirrer was charged 12 mL of DMF to the stirred solvent was added K2CO3 (2.2 g, 16 mmol), 4-methoxyphenol (1 g, 8 mmol) and ethyl bromoacetate (1.1 mL, 9.6 mmol) Then the reaction mixture was Stirred at RT for 5 h. After completion of the reaction (reaction monitored by TLC), reaction mixture was concentrated and extracted with ethyl acetate. Then the organic layer was dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to get the compound (2 g, Yield: 90%).

Workup

  1. customTo a 100 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC), reaction mixture
  3. concentrationwas concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThen the organic layer was dried over anhydrous Na2SO4
  6. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-edc33ed8b74549a89a622de8be1bc3bf
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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