Reaktion #155874

Reaktionsgleichung

(Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine

(E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine

potassium carbonate

→

6-bromo-3-ethyl-1-phenyl-1H-indazole

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 1000-mL 3-necked round-bottom flask, was placed
2. 2
   EinengenThe resulting mixture was concentrated under vacuum
3. 3
   workup.ADDITIONThe resulting solution was diluted with water (500 mL)
4. 4
   ExtraktionThe resulting solution was extracted with ethyl acetate (2×300 mL)
5. 5
   WaschenThe resulting mixture was washed with water (2×300 mL) and brine (1×300 mL)
6. 6
   TrocknenThe resulting mixture was dried over anhydrous sodium sulfate
7. 7
   Einengenconcentrated under vacuum

Vorschrift

Into a 1000-mL 3-necked round-bottom flask, was placed a solution of (Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine (44.3 g, 138.01 mmol, 1.00 equiv) in N,N-dimethylformamide (400 mL), potassium carbonate (83 g, 601.45 mmol, 4.40 equiv). The resulting solution was stirred for 2 days at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with water (500 mL). The resulting solution was extracted with ethyl acetate (2×300 mL) and the organic layers combined. The resulting mixture was washed with water (2×300 mL) and brine (1×300 mL). The resulting mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50) to yield 6-bromo-3-ethyl-1-phenyl-1H-indazole as a yellow solid.

Quelle