Ethyl bromoacetate → Acetic acid, 2-(2-chloro-4-nitrophenoxy)-, ethyl ester

HRID 1160428Notes

Reaction equation

HRID 1160428 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 12074Nitrofungin

Product 1

HCID 17370879Acetic acid, 2-(2-chloro-4-nitrophenoxy)-, ethyl esterYield 64.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-chloro-4-nitrophenol (63.6 g, 0.367 mol), ethyl bromoacetate (67.0 g, 0.4 mol), potassium carbonate (60.7 g, 0.44 mol) and 2-butanone (400 mL) was refluxed under stirring for 10 h, then filtered and the solvent was evaporated. The residue was fractionated yielding 61.1 g (64%) of 2-chloro-4-nitrophenoxyacetic acid ethyl ester, b.p. 150° C./40 Pa.

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-20dc97ffeb634d2287b773e6e7157b82
Source dataset
uspto-grants-2010_10
Patent number
US07816385B2

Reaction notes

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