Ethyl bromoacetate → Ethyl (3,5-dichloro-4-formylphenoxy)acetate

HRID 856965Notes

Reaction equation

HRID 856965 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5])[O:10][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

Product 1

HCID 71373969Ethyl (3,5-dichloro-4-formylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.87 g (15 mmol) A1, 2.76 g (16.5 mmol) ethyl bromoacetate and 2.90 g (21 mmol) potassium carbonate in 50 ml dry acetone were stirred for 3 h at 60° C. After filtration and removal of the solvent the residue was purified by column chromatography on Silica (ethyl acetate/methanol 100:2). Yield: 3.5.5 g (86 %) A2, colorless solid.

Workup

  1. filtrationAfter filtration and removal of the solvent the residue
  2. customwas purified by column chromatography on Silica (ethyl acetate/methanol 100:2)

Sources & evidence

ORD record
ord-6f5b0045d096459187a14b2011eb52ff
Source dataset
uspto-grants-2006_12
Patent number
US07144889B2

Reaction notes

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