Reaction #86912

Reaction equation

Iodine

4-aminobenzonitrile

→

title compound

Yield 36.0%

4-amino-3-iodobenzonitrile

Yield 36.0%

Solvents

ethanol

Conditions

Workup

1. 1
   Filtrationfiltered over celite
2. 2
   OtherThe volatiles were removed under reduced pressure
3. 3
   Otherthe residue was partitioned between ethyl acetate
4. 4
   WashThe organic layer was washed with brine
5. 5
   Otherdried
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane)

Procedure

Iodine (0.645 g; 2.54 mmol) was added to a stirred mixture of silver sulphate (0.791 g; 2.54 mmol) and 4-aminobenzonitrile (0.300 g; 2.54 mmol) in ethanol (10 mL). The reaction mixture was stirred at room temperature for 18 hours and filtered over celite. The volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium thiosulphate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The crude residue was purified by flash chromatography on silica gel (eluent 2 to 40% ethyl acetate in heptane) to afford 0.222 g (36%) of the title compound as a white solid.

Source