Cesium carbonate → HCID 66680479, compound

HRID 537673Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]2[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]2=[O:17])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][C:28]=1[F:34]>FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O.C1(C)C=CC=CC=1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][C:2]2[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]3[C:13](=[O:14])[CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10][C:9]3=[O:17])[CH:7]=2)=[CH:29][C:28]=1[F:34]

Participants

Conditions

Temperature: 170 °C

Procedure

To a mixture of 2-(5-bromo-2-ethylphenyl)-5,5-dimethylcyclohexane-1,3-dione (0.236 g, 0.73 mmol), cesium carbonate (0.477 g, 1.46 mmol), 4-chloro-3-fluorophenol (0.535 g, 3.65 mmol), copper (II) trifluoromethanesulfonate (0.012 g, 0.04 mmol) and powdered 3 Å molecular sieves (0.300 g) is added anhydrous toluene (4 ml). After purging with nitrogen the reaction mixture is heated at 170° C. for 1 hour under microwave irradiation, then allowed to cool to room temperature. After quenching with 2M aqueous hydrochloric acid the crude product is extracted into dichloromethane (×2) and the phases are separated. Organic solvents are removed in vacuo and the crude product is purified by preparative reverse-phase HPLC to afford 2-[5-(4-chloro-3-fluorophenoxy)-2-ethylphenyl]-5,5-dimethylcyclohexane-1,3-dione as a white solid.

Workup

customAfter purging with nitrogen the reaction mixture
temperatureto cool to room temperature
customAfter quenching with 2M aqueous hydrochloric acid the crude product
extractionis extracted into dichloromethane (×2)
customthe phases are separated
customOrganic solvents are removed in vacuo
customthe crude product is purified by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-4bc03de0a9b4411da06912d764468906
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865623B2

Reaction notes

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