Potassium Carbonate → Ethyl 2,2-Bis-(3-iodophenoxy)acetate

HRID 974760Notes

Reaction equation

HRID 974760 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])C(OCC)=O.[C:21](=[O:24])([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:19]([O:18][C:16](=[O:17])[CH:10]([O:24][C:21]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 69637Diethyl bromomalonate

Product 1

HCID 19959850Ethyl 2,2-Bis-(3-iodophenoxy)acetateYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 40.0 g (0.18 mol) of 3-iodophenol, 33.6 ml (0.18 mol) of diethyl bromomalonate and 27.63 g (0.2 moles) of milled anhydrous potassium carbonate in 250 ml dry N,N-dimethylformamide was heated at 110°-120° C. under argon for 14 hours. The mixture was cooled and concentrated in vacuo. The resulting residue was combined with 600 ml of ice-cold water and the oily product was extracted with ethyl acetate (4×150 ml). The combined ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to an orange oil. The orange oil was purified by chromatography (eluted by 5% methylene chloride in hexanes to 50% methylene chloride in hexanes) to yield 8.1 g (8.5%) of the desired product as a tan oil.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. extractionthe oily product was extracted with ethyl acetate (4×150 ml)
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo to an orange oil
  6. customThe orange oil was purified by chromatography (eluted by 5% methylene chloride in hexanes to 50% methylene chloride in hexanes)

Sources & evidence

ORD record
ord-6d3e7daf390c4464a942f6ff74c91fc5
Source dataset
uspto-grants-1997_03
Patent number
US05607660

Reaction notes

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