Iodine → 4-Amino-3-fluoro-5-iodobenzonitrile
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[F:10].[I:11]I>CCO.[O-]S([O-])(=O)=O.[Ag+].[Ag+]>[NH2:1][C:2]1[C:9]([I:11])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[F:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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.
Workup
- filtrationThe mixture was filtered
- concentrationconcentrated
- dissolutionThe residue was dissolved in EtOAc
- washwashed (sat. Na2S2O3×3)
- dry with materialThe organic layer was dried (Na2SO4)
- concentrationconcentrated
- customThe residue was purified by flash column chromatography (SiO2, 95:5 to 70:30 cyclohexane/EtOAc)
Sources & evidence
- ORD record
- ord-0440163263d74d16a1464a8da506aac9
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440929B2
Reaction notes
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