Reaktion #746813

Reaktionsgleichung

1-(4-bromophenyl)-2-cyclohexylidenehydrazine

HCl

sodium hydroxide

→

3-bromo-6,7,8,9-tetrahydro-5H-carbazole

Ausbeute 193.4%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturUpon completion, the reaction mixture was cooled down to room temperature
2. 2
   ExtraktionThe resulting mixture was then extracted with ethyl acetate (5×100 mL)
3. 3
   TrocknenThe combined organic layers were dried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered off
5. 5
   Einengenconcentrated on a rotary evaporator
6. 6
   SonstigeThe residue was purified by a silica gel column chromatography
7. 7
   Wascheneluted with ethyl acetate/petroleum ether (1/10)

Vorschrift

A 250-mL round-bottomed flask was charged with 1-(4-bromophenyl)-2-cyclohexylidenehydrazine (11 g, 41.35 mmol, 1.00 equiv) and conc. HCl (150 mL). The resulting mixture was heated to 60° C. in an oil bath for 4 hours. The reaction progress was monitored by TLC (EtOAc:PE=1:1). Upon completion, the reaction mixture was cooled down to room temperature. The pH was adjusted to 8 with aqueous sodium hydroxide. The resulting mixture was then extracted with ethyl acetate (5×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1/10) affording 3-bromo-6,7,8,9-tetrahydro-5H-carbazole as yellow solid (10 g, 97%).

Quelle