2,2'-Bipyridine → (E)-1-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)-1H-1,2,4-triazole

HRID 1502765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502765
Br[CH:2]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[CH:8]=1)[C:3]([F:6])([F:5])[F:4].[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:19][CH:18]=1)=[CH2:16].N1C=CC=CC=1C1C=CC=CN=1>ClC1C=CC=CC=1Cl.Cl[Cu]>[Cl:14][C:9]1[CH:8]=[C:7]([CH:2]([C:3]([F:6])([F:5])[F:4])/[CH:16]=[CH:15]/[C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[N:26][CH:25]=[N:24]3)=[CH:21][CH:22]=2)[CH:12]=[C:11]([Cl:13])[CH:10]=1

Komponenten

6

Edukt 3

HCID 14742,2'-BipyridineHCID 585499641-(4-vinylphenyl)-1H-1,2,4-triazoleHCID 866751181-(1-Bromo-2,2,2-trifluoroethyl)-3,5-dichlorobenzene

Produkt 1

HCID 86675223(E)-1-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)-1H-1,2,4-triazoleAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

To a stirred solution of 1-(1-bromo-2,2,2-trifluoro-ethyl)-3,5-dichloro-benzene (2.0 g, 6.51 mmol) in 1,2-dichlorobenzene (25 mL), were added 1-(4-vinyl-phenyl)-1H-[1,2,4]triazole (2.22 g, 13.0 mmol), CuCl (64 mg, 0.65 mmol) and 2,2-bipyridyl (0.2 g, 1.3 mmol). The resultant reaction mixture was degassed with argon for 30 min, then stirred at 180° C. for 24 h. After completion of reaction (TLC), the reaction mixture was cooled to ambient temperature and filtered and the filtrate concentrated under reduced pressure. Purification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether) afforded the title compound as an off-white solid (0.8 g, 32%): mp 93-97° C.; 1H NMR (300 MHz, CDCl3) δ 8.56 (s, 1H), 8.11 (s, 1H), 7.68 (d, J=8.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.38 (t, J=1.8 Hz, 1H), 7.29 (s, 2H), 6.62 (d, J=15.6 Hz, 1H), 6.42 (dd, J=15.6, 8.2 Hz, 1H), 4.15 (m, 1H); ESIMS m/z 398.05 ([M+H]+).

Aufarbeitung

  1. customThe resultant reaction mixture
  2. customwas degassed with argon for 30 min
  3. customAfter completion of reaction (TLC)
  4. temperaturethe reaction mixture was cooled to ambient temperature
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customPurification by flash chromatography (SiO2, 100-200 mesh; 25-30% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-cb6d6bdf239f404da3e4f86dbe7e7d97
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09210927B2

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