تفاعل #155714

معادلة التفاعل

hydrochloric acid

2-amino-1-bromophenanthrene

sodium nitrite

phosphinic acid

→

1-bromophenanthrene

المردود 66.1%

المذيبات

water

water

THF

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe 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
   أخرىa solid was separated by filtration
5. 5
   أخرىThe resultant solid was purified by silica gel column chromatography

الإجراء التجريبي

First, 12.0 g of 2-amino-1-bromophenanthrene were dissolved in 75 mL of THF, and then 450 mL of concentrated hydrochloric acid and 150 mL of water were added to the solution. The reaction solution was cooled with ice, and then a solution of 4.5 g of sodium nitrite in 23 mL of water was dropped to the solution. After the mixture had been stirred for 1 hour under ice cooling, 225 mL 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, 1 L of water were added to the solution, and a solid was separated by filtration. The resultant solid was purified by silica gel column chromatography. Thus, 7.5 g of 1-bromophenanthrene were obtained (in 66% yield).

المصدر