3,4-Dichlorophenol → 2-[5-(3,4-Dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione

HRID 339469노트

반응식

HRID 339469 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1.[Cl:17][C:18]1[CH:19]=[C:20]([OH:25])[CH:21]=[CH:22][C:23]=1[Cl:24].C(=O)([O-])[O-].[Cs+].[Cs+]>[O-]S(C(F)(F)F)(=O)=O.[Cu+2].[O-]S(C(F)(F)F)(=O)=O.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:25][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1

참가 물질

6

반응물 3

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 666773502-(5-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

생성물 1

HCID 666767552-[5-(3,4-Dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione

시약·촉매·용매 2

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 1140Toluene용매

반응 조건

온도
160 °C

실험 절차

To a mixture of 2-(5-bromo-2-ethylphenyl)cyclopentane-1,3-dione (0.200 g, 0.71 mmol), 3,4-dichlorophenol (0.577 g, 3.56 mmol), cesium carbonate (0.502 g, 1.42 mmol), copper triflate (13 mg, 0.04 mmol) and activated (powdered) 5 Å molecular sieves (0.400 g) is added anhydrous toluene (2.5 ml). The reaction mixture is purged with nitrogen then heated at 160° C. for 1 hour under microwave irradiation. After cooling to room temperature dichloromethane is added and mixture is quenched with 2M aqueous hydrochloric acid then filtered. The organic phase is concentrated under reduced pressure to give a crude oil which is purified by preparative reverse-phase HPLC to afford 2-[5-(3,4-dichlorophenoxy)-2-ethylphenyl]cyclopentane-1,3-dione.

후처리

  1. customThe reaction mixture is purged with nitrogen
  2. temperatureAfter cooling to room temperature dichloromethane
  3. additionis added
  4. custommixture is quenched with 2M aqueous hydrochloric acid
  5. filtrationthen filtered
  6. concentrationThe organic phase is concentrated under reduced pressure
  7. customto give a crude oil which
  8. customis purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-f360613ab512475eb52e2deac87ff588
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895474B2

반응 노트

불러오는 중…