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

HRID 339469Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-f360613ab512475eb52e2deac87ff588
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895474B2

Reaction notes

Loading…