Reaction #1994252

Reaction equation

water

carbazole

sodium hydroxide

allylbromide

→

N-Allylcarbazole

Solvents

dimethylsulfoxide

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe ethyl acetate layer was washed with water
3. 3
   Concentrationconcentrated
4. 4
   OtherThe crude product was purified

Procedure

A mixture of 10.85 g (65.0 mmol) of carbazole, 2.60 g (65.0 mmol) of sodium hydroxide and 6.1 mL (72.0 mmol) of allylbromide in 100 mL dimethylsulfoxide was heated to 60° C. for 5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then concentrated. The crude product was purified using column chromatography (silica, 1:4 dichloromethane:hexane). Yield: 9.85 g (73%).

Source