Iodine → 4-Amino-3-fluoro-5-iodobenzonitrile

HRID 59936

Reaktionsgleichung

Reaktionsgleichung von HRID 59936
[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]

Komponenten

5

Edukt 2

HCID 807IodineHCID 27564314-Amino-3-fluorobenzonitrile

Produkt 1

HCID 442031204-Amino-3-fluoro-5-iodobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159865Silver sulfateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed (sat. Na2S2O3×3)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (SiO2, 95:5 to 70:30 cyclohexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-0440163263d74d16a1464a8da506aac9
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440929B2

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