Diphenylamine → 4-Bromodiphenylamine

Participants

Reaction Steps

In a 1000-mL Erlenmeyer flask were placed 20 g (118.1 mmol) of diphenylamine, 500 mL of chloroform, and an ellipsoidal stirring chip. In a 500-mL beaker was placed 113.8 g (236.2 mmol) of tetrabutylammoniumtribromide (TBABr3), which was dissolved in 200 mL of chloroform added later. The resulting solution was added dropwise to the chloroform-diphenylamine solution, and the mixture was stirred for 20 hours at room temperature in the air. Then, the chloroform-diphenylamine solution was transferred to a 1000-mL separatory funnel and washed seven times with 100 mL of saturated aqueous solution of sodium thiosulfate. The organic layer was transferred to a 1000-mL Erlenmeyer flask and then dehydrated with 100 g of anhydrous magnesium sulfate. With the anhydrous magnesium sulfate removed by filtration, the chloroform solution was transferred to a 1000-mL eggplant-shaped flask and freed of chloroform by means of an evaporator. The resulting crude product was purified by means of a silica gel column (hexane:chloroform=1:1) (Yields: 70%).

Provenance & Evidence