Sodium Carbonate → 4-(4-Trifluoromethylphenyl)-1-indanone

HRID 1533113

Reaktionsgleichung

Reaktionsgleichung von HRID 1533113
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[CH:16][CH:15]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 987131-Indanone, 4-bromo-HCID 27343894-(Trifluoromethyl)phenylboronic acid

Produkt 1

HCID 217020674-(4-Trifluoromethylphenyl)-1-indanone

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

6.33 g (0.03 mol) of 4-bromo-1-indanone and 5.7 g (0.03 mol) of 4-trifluoromethylphenylboronic acid are suspended with 6.36 g (0.06 mol) of sodium carbonate in a mixture of 100 ml of toluene with 20 ml of ethanol and 20 ml of water. Under an argon atmosphere, 320 mg (1.42 mmol) of palladium(II) acetate and 787 mg (3 mmol) of triphenylphosphine are added, and the mixture is boiled under reflux for 5 h. After the reaction is complete, the ethanol content is evaporated off in vacuo, 50 ml of 0.5 N sodium hydroxide solution are added to the residue, and the mixture is stirred and filtered with suction through a clarifying layer. The organic phase of the filtrate is separated off, shaken 3× with 50 ml of water each time, shaken once with saturated brine, dried over sodium sulfate and concentrated in vacuo. The crude product is chromatographed on silica gel with n-heptane/ethyl acetate 3/1. 4-(4-Trifluoromethylphenyl)-1-indanone is obtained with a melting point of 75-78° C.

Aufarbeitung

  1. temperatureunder reflux for 5 h
  2. customthe ethanol content is evaporated off in vacuo, 50 ml of 0.5 N sodium hydroxide solution
  3. additionare added to the residue
  4. filtrationfiltered with suction through a clarifying layer
  5. customThe organic phase of the filtrate is separated off
  6. stirringshaken 3× with 50 ml of water each time
  7. stirringshaken once with saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product is chromatographed on silica gel with n-heptane/ethyl acetate 3/1

Quellen und Nachweise

ORD-Eintrag
ord-375b9fabe5db42ac91164e39087ad2d0
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207689B1

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