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

HRID 339469ノート

反応式

HRID 339469 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 2734996copper(II) trifluoromethanesulfonate触媒HCID 1140Toluene溶媒

反応条件

温度
160 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f360613ab512475eb52e2deac87ff588
出典データセット
uspto-grants-2014_11
特許番号
US08895474B2

反応ノート

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