1,10-Phenanthroline → HCID 86675809, Verbindung

HRID 59873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59873
[F:1][C:2]([F:19])([O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[N:17][N:18]=2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].I[C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O.[Cu]I>[F:19][C:2]([F:1])([O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:15][C:16]([C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=3)=[N:17][N:18]=2)=[CH:12][CH:13]=1)[C:3]([F:6])([F:5])[F:4]

Komponenten

8

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 69273Methyl 4-iodobenzoateHCID 866758082-(4-(Perfluoroethoxy)phenyl)-1,3,4-oxadiazole

Produkt 1

HCID 86675809HCID 86675809, VerbindungAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazole (2.186 g, 7.80 mmol), methyl 4-iodobenzoate (3.07 g, 11.70 mmol), copper(I) iodide (0.28 g, 1.47 mmol), 1,10-phenanthroline (0.30 g, 1.67 mmol), and cesium carbonate (2.54 g, 7.80 mmol) in anhydrous DMSO (20 mL) was heated at 100° C. for 18 hours. The reaction was cooled, diluted with water, and extracted three times with EtOAc. The organic layers were dried over anhydrous sodium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-50% EtOAc/hexanes) provided methyl 4-(5-(4-(perfluoroethoxy)phenyl)-1,3,4-oxadiazol-2-yl)benzoate as a white solid (1.08 g, 33%): mp 185-191° C.; 1H NMR (400 MHz, CDCl3) δ 8.25-8.19 (m, 6H), 7.41 (t, J=9.4 Hz, 2H), 3.98 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −85.96, −85.98, −87.79; ESIMS m/z 415 ([M+H]+).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted three times with EtOAc
  3. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customPurification by flash chromatography (0-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1ee9304f1fa44a2485a85ac562afe37e
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440964B2

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