2,4-Dichlorophenol → HCID 66680198, compound

HRID 537688Notes

Reaction equation

HRID 537688 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH:20]2[CH2:22][CH2:21]2)=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])[CH:7]=1.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[OH:31].C(=O)([O-])[O-].[Cs+].[Cs+]>FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O.C1(C)C=CC=CC=1>[CH:20]1([C:5]2[CH:4]=[CH:3][C:2]([O:31][C:25]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=3[Cl:23])=[CH:7][C:6]=2[CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:17])([CH3:18])[C:9]2=[O:19])[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 84492,4-DichlorophenolHCID 10796Cesium carbonateHCID 66678882HCID 66678882, compound

Product 1

HCID 66680198HCID 66680198, compound

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of 4-(5-bromo-2-cyclopropylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.208 g, 0.57 mmol), 2,4-dichlorophenol (473 mg, 2.85 mmol), cesium carbonate (0.400 g, 1.13 mmol), copper (II) trifluoromethanesulfonate (10 mg, 0.03 mmol) and activated (powdered) 5 Å molecular sieves (0.330 g) is added anhydrous toluene (3.5 ml). The mixture is purged with nitrogen then heated at 160° C. for 1 hour under microwave irradiation. After cooling to room temperature the reaction mixture is diluted with dichloromethane and 2M hydrochloric acid, then filtered and the organic phase separated. After concentration in vacuo the residue is purified by preparative reverse phase HPLC to afford 4-[2-cyclopropyl-5-(2,4-dichlorophenoxy)-phenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

Workup

  1. customThe mixture is purged with nitrogen
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. additionis diluted with dichloromethane and 2M hydrochloric acid
  4. filtrationfiltered
  5. customthe organic phase separated
  6. concentrationAfter concentration in vacuo the residue
  7. customis purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-49dd46b0e7344c65b4e256222159153b
Source dataset
uspto-grants-2014_10
Patent number
US08865623B2

Reaction notes

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