Acetylacetone → HCID 90412515, Verbindung

HRID 573943

Reaktionsgleichung

Reaktionsgleichung von HRID 573943
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(=O)[CH2:34][C:35](=[O:37])[CH3:36]>CS(C)=O.[Cu]I>[F:21][C:20]([F:23])([F:22])[O:19][C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH:11]=[N:12][C:8]([C:5]3[CH:6]=[CH:7][C:2]([CH2:34][C:35](=[O:37])[CH3:36])=[CH:3][CH:4]=3)=[N:9]2)=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 31261AcetylacetoneHCID 62657Potassium Phosphate, TribasicHCID 904040773-(4-bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazole

Produkt 1

HCID 90412515HCID 90412515, VerbindungAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

3-(4-Bromophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C52) (11 g, 29 mmol), copper(I) iodide (0.55 g, 2.9 mmol), potassium phosphate (18 g, 86 mmol), and pentane-2,4-dione (8.9 mL, 86 mmol) were dissolved in dimethylsulfoxide (120 mL) in a 500 mL round bottomed flask. The reaction was heated at 110° C. for 19 hours. The solution was cooled to room temperature and then quenched with hydrogen chloride (2 N). The excess base was removed by gravity filtration and the filtrate was extracted with ethyl acetate. The organics were washed with water, extracted, dried, and concentrated. Purification by flash column chromatography using 0-30% ethyl acetate/hexanes afforded the title compound as a pure orange solid (3.7 g, 35%): 1H NMR (400 MHz, CDCl3) δ 8.56 (s, 1H), 8.17 (d, J=8.2 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.39 (dt, J=8.1, 1.0 Hz, 2H), 7.33 (dd, J=8.1, 0.6 Hz, 2H), 3.76 (s, 2H), 2.19 (s, 3H); ESIMS m/z 361 ([M]+).

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. customquenched with hydrogen chloride (2 N)
  3. customThe excess base was removed by gravity filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe organics were washed with water
  6. extractionextracted
  7. customdried
  8. concentrationconcentrated
  9. customPurification by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f8711a210c5043c3aac2ff4b91a740c7
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029560B2

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