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

HRID 53498

반응식

HRID 53498 반응식
[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]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 69637Diethyl bromomalonate

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-aba6f21e242c4e97988ea0ec9c79dcb5
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620677

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