Ethyl bromoacetate → HCID 13204948, compound

HRID 221214Notes

Reaction equation

HRID 221214 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 15285Phenol, 4-methoxy-2-nitro-

Product 1

HCID 13204948HCID 13204948, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-methoxy-2-nitrophenol 9 (1.69 g, 0.01 mol), potassium carbonate (2.76 g, 0.02 mol) and ethyl bromoacetate 6d (1.1 mL, 0.01 mol) in 20 mL anhydrous acetone was refluxed for overnight (12 h). The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was evaporated, the residue was diluted with water and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated to give ethyl 2-(4-methoxy-2-nitrophenoxy)acetate 11 which was purified by silica gel column chromatography using 0-50% gradient of hexane and ethyl acetate.

Workup

  1. temperaturewas refluxed for overnight (12 h)
  2. customThe reaction mixture was evaporated
  3. additionthe residue was diluted with water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-5d4227879d9b4480b81e0490b2b60295
Source dataset
uspto-grants-2012_06
Patent number
US08207163B2

Reaction notes

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