Reaktion #796133

Reaktionsgleichung

3-p-tolyl-1H-[1,2,4]triazole

4-bromophenyl pentafluoroethyl ether

Cs2CO3

8-hydroxyquinoline

HCl

→

1-(4-pentafluoroethyloxy-phenyl)-3-p-tolyl-1H-[1,2,4]triazole

Ausbeute 62.1%

Lösungsmittel

Ether

H2O

DMF H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was then cooled
2. 2
   Filtrationfiltered
3. 3
   Sonstigebefore separating layers
4. 4
   SonstigeThe organic layer was dried
5. 5
   Einengenconcentrated
6. 6
   Temperaturthe resulting gummy solid was heated with hexanes (100 mL)
7. 7
   SonstigeThe hot hexane layer was decanted from insoluble residue
8. 8
   Temperaturthe resulting solution cooled to 0° C.
9. 9
   Filtrationthe precipitated solid was filtered
10. 10
    Sonstigeair-dried

Vorschrift

A solution of 3-p-tolyl-1H-[1,2,4]triazole (4.85 g, 30.5 mmol), 4-bromophenyl pentafluoroethyl ether (10.0 g, 34.4 mmol), Cs2CO3 (25 g, 77 mmol), CuI (1.25 g, 6.5 mmol) and 8-hydroxyquinoline (0.35 g, 2.4 mmol) in 9:1 DMF/H2O (50 mL) was stirred vigorously and heated to 130° C. (internal temperature) for 20 h. The solution was then cooled, poured into H2O, and acidified with 2 N HCl to pH 2. Ether (250 mL) was then added and the solution was shaken and filtered before separating layers. The organic layer was dried and concentrated, and the resulting gummy solid was heated with hexanes (100 mL). The hot hexane layer was decanted from insoluble residue, the resulting solution cooled to 0° C. and the precipitated solid was filtered and air-dried to furnish 1-(4-pentafluoroethyloxy-phenyl)-3-p-tolyl-1H-[1,2,4]triazole (7.0 g, 61% based on starting triazole) as an off-white solid: mp 130-132° C.; ESIMS m/z 370.8 (M+H).

Quelle