Potassium Carbonate → 1-((1,1'-Biphenyl)-3-yl)ethan-1-one

HRID 2296979

Reaktionsgleichung

Reaktionsgleichung von HRID 2296979
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)=[O:12].C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([C:13]1[CH:14]=[C:15]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=[CH:17][CH:18]=1)(=[O:12])[CH3:10]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 165023'-BromoacetophenoneHCID 66827Phenylboronic Acid

Produkt 1

HCID 2585681-((1,1'-Biphenyl)-3-yl)ethan-1-oneAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A suspension of 6.71 g (55 mmol) of phenylboronic acid, 9.95 g (50 mmol) of 3-bromoacetophenone, 30 mg (0.13 mmol) of palladium acetate, 17.28 g (125 mmol) of potassium carbonate and 16.12 g (50 mmol) of tetrabutylammonium bromide in 55 ml of water was vigorously stirred under a stream of nitrogen and then stirred at 70° C. under an atmosphere of nitrogen for 75 minutes. Water was added to the reaction mixture and the mixture was extracted with tert-butyl methyl ether. Then, the organic layer was dried and concentrated. The residue (10.23 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=7:1) to obtain 9.82 g of 3-acetylbiphenyl as oil.

Aufarbeitung

  1. stirringstirred at 70° C. under an atmosphere of nitrogen for 75 minutes
  2. extractionthe mixture was extracted with tert-butyl methyl ether
  3. customThen, the organic layer was dried
  4. concentrationconcentrated
  5. washThe residue (10.23 g) was subjected to silica gel column chromatography (eluted with n-hexane:ethyl acetate=7:1)

Quellen und Nachweise

ORD-Eintrag
ord-c69843e77fd0413b94f64d8b8427e440
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489487B1

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