Reaction #88214

Reaction equation

4-amino-3-fluorobenzonitrile

I2

→

desired product

4-Amino-3-fluoro-5-iodo-benzonitrile

Solvents

EtOH

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered
2. 2
   Concentrationconcentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
4. 4
   Washwashed (sat. Na2S2O3×3)
5. 5
   DryingThe organic layer was dried (Na2SO4)
6. 6
   Concentrationconcentrated
7. 7
   OtherThe residue was purified by flash column chromatography (SiO2, 95:5 to 70:30 cyclohexane/EtOAc)

Procedure

A mixture of 4-amino-3-fluorobenzonitrile (147 mmol), I2 (147 mmol) and Ag2SO4 (147 mmol) in EtOH (700 mL) was stirred at room temperature for 1.5 h. The mixture was filtered and concentrated. The residue was dissolved in EtOAc and washed (sat. Na2S2O3×3). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (SiO2, 95:5 to 70:30 cyclohexane/EtOAc) to yield the desired product.

Source