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

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

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.