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

HRID 1728296Notes

Reaction equation

HRID 1728296 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>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:10]([O:24][C:21]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

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. Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. FAB/MS: M+ 524. Calculated for C16H14I2O4 : C, 36.67 H, 2.69; I, 48.43. Found: C, 36.92; H, 2.65; I, 48.24.

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-6b3a08beb94c49f7b077ea1752c97c2b
Source dataset
uspto-grants-1994_07
Patent number
US05326553

Reaction notes

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