Reaktion #58834

Reaktionsgleichung

KOH

1-(3-bromophenyl)butan-1-one

diglyme

hydrazine

→

1-bromo-3-butylbenzene

Ausbeute 86.4%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at 150° C. for 6 hours
2. 2
   Temperaturcooled to room temperature
3. 3
   Extraktionextracted with ethyl ether
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated under vacuum
6. 6
   SonstigePurification of the resultant residue on silica gel (ISCO)

Vorschrift

A mixture of 1-(3-bromophenyl)butan-1-one (1.0 g, 4.4 mmol) and diglyme (10 mL) was treated with hydrazine (1.49 g, 44 mmol), stirred at 100° C. for 2 h, treated with KOH (1.23 g, 22 mmol), stirred at 150° C. for 6 hours, cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated under vacuum. Purification of the resultant residue on silica gel (ISCO) using hexanes as the eluting solvent gave 1-bromo-3-butylbenzene as a clear oil (0.81 g, 86% yield).

Quelle