Reaktion #155686

Reaktionsgleichung

hydrochloric acid

2-amino-1-bromophenanthrene

sodium nitrite

phosphinic acid

→

1-bromophenanthrene

Ausbeute 66.1%

Lösungsmittel

water

water

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction solution was cooled with ice
2. 2
   workup.STIRRINGThe reaction solution was stirred for 30 minutes under ice cooling
3. 3
   workup.STIRRINGwas then continuously stirred at room temperature for 17 hours
4. 4
   Sonstigea solid was obtained through separation by filtration
5. 5
   SonstigeThe resultant solid was purified by silica gel column chromatography

Vorschrift

First, 120 g of 2-amino-1-bromophenanthrene were dissolved in 750 mL of THF, and then 4.5 L of concentrated hydrochloric acid and 1.5 L of water were added to the solution. The reaction solution was cooled with ice, and then a solution of 45 g of sodium nitrite in 230 mL of water was dropped to the solution. After the mixture had been stirred for 1 hour under ice cooling, 2.25 L of a 50% aqueous solution of phosphinic acid were added to the mixture. The reaction solution was stirred for 30 minutes under ice cooling, and was then continuously stirred at room temperature for 17 hours. Subsequently, 10 L of water were added to the solution, and a solid was obtained through separation by filtration. The resultant solid was purified by silica gel column chromatography. Thus, 75 g of 1-bromophenanthrene were obtained (in 66% yield).

Quelle