Cesium carbonate → HCID 49765295, compound

HRID 537672Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][C:4]=1[CH:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]1=[O:17])[CH3:2].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[C:4]([CH:10]3[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C:11]3=[O:17])[CH:5]=2)=[C:21]([F:26])[CH:20]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a mixture of 2-(2-ethyl-5-iodophenyl)cyclohexane-1,3-dione (0.250 g, 0.73 mmol), 4-chloro-2-fluorophenol (0.535 g, 3.65 mmol) and cesium carbonate (0.477 g, 1.46 mmol) is added powdered 3 Å molecular sieves (0.300 g) and copper (II) trifluoromethanesulfonate (0.012 g, 0.037 mmol). After degassing with nitrogen anhydrous toluene (4 ml) is added, and the suspension is heated at 160° C. for 1 hour under microwave irradiation. The reaction mixture is acidified with 2M aqueous hydrochloric acid and extracted with dichloromethane (×2). The organic phase is separated then evaporated under reduced pressure to yield a crude product which is purified by preparative reverse-phase HPLC to afford 2-[5-(4-chloro-2-fluoro-phenoxy)-2-ethylphenyl]cyclohexane-1,3-dione.

Workup

additionis added
customAfter degassing with nitrogen anhydrous toluene (4 ml)
additionis added
extractionextracted with dichloromethane (×2)
customThe organic phase is separated
customthen evaporated under reduced pressure
customto yield a crude product which
customis purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-415461a847bf4b7c93a7e0f205e5b957
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865623B2

Reaction notes

Loading…