N-Iodosuccinimide → 5-Bromo-4-chloro-2-iodoaniline

HRID 588802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588802
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C1C(=O)N([I:17])C(=O)C1>CC(O)=O>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([I:17])=[C:4]([NH2:9])[CH:3]=1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 128437223-Bromo-4-chloroaniline

Produkt 1

HCID 509995085-Bromo-4-chloro-2-iodoanilineAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-4-chlorobenzenamine (10.0 g, 48.5 mmol) in CH3COOH (50 mL), NIS (10.9 g, 48.5 mmol) was added in portions and the resulting mixture was stirred at room temperature for 16 h. The mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=50:1) to afford the desired product (2.5 g, 15.5% yield). ESI-MS m/z: 329.9 [M−H]−.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-959f52af961e4af7bb29aa1f1d0e7f23
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227978B2

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