Reaction #2320135

Reaction equation

potassium hydroxide

9-[N,N-bis(4-methylphenyl)amino]anthracene

sodium thiosulfate

bromine

→

9-[N,N-bis(4-methylphenyl)amino]-10-bromoanthracene

Yield 83.3%

Solvents

water

dioxane

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the mixture dropwise
2. 2
   workup.STIRRINGthe whole was stirred for 30 minutes
3. 3
   workup.STIRRINGthe whole was stirred for 1 hour
4. 4
   FiltrationThe product was filtrated
5. 5
   Washwashed with methanol
6. 6
   OtherThe product was recrystallized

Procedure

In a stream of nitrogen, 11.2 g (30 mmol) of 9-[N,N-bis(4-methylphenyl)amino]anthracene was dissolved in 100 ml of dioxane, and the whole was stirred at room temperature. Then, 1.68 g (30 mmol) of potassium hydroxide dissolved in 3 ml of water was added to the mixture dropwise. 5.75 g of bromine was added thereto, and the whole was stirred for 30 minutes. A 5% aqueous solution of sodium thiosulfate was added to the mixture, and the whole was stirred for 1 hour. The product was filtrated and washed with methanol. The product was recrystallized by using toluene, to thereby obtain 11.3 g of 9-[N,N-bis(4-methylphenyl)amino]-10-bromoanthracene.

Source