3,5-Dichloroaniline → 3,5-Dichloro-2-iodoaniline

HRID 129847

Reaktionsgleichung

Reaktionsgleichung von HRID 129847
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[I:10]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)Cl>[I:10][C:3]1[C:2]([Cl:1])=[CH:8][C:7]([Cl:9])=[CH:6][C:4]=1[NH2:5]

Komponenten

5

Edukt 3

HCID 122813,5-DichloroanilineHCID 120273N-IodosuccinimideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 100169433,5-Dichloro-2-iodoanilineAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21922555Acetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

Dissolve 3,5-dichloroaniline (10 g, 61.5 mmol) in 1:1 acetic acid/methylene chloride (200 mL). Add N-iodosuccinimide (16.9 g, 61.5 mmol) as a solid and stir at room temperature in the absence of light for 8 hours. Pour the solution into saturated sodium hydrogen carbonate (200 mL) and extract into methylene chloride (100 mL). Wash with saturated sodium hydrogen carbonate (200 mL), dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography to give the title compound (8.1 g, 45%); mp 61°-63° C.

Aufarbeitung

  1. extractionextract into methylene chloride (100 mL)
  2. washWash with saturated sodium hydrogen carbonate (200 mL)
  3. dry with materialdry (MgSO4)
  4. customevaporate the solvent in vacuo
  5. customPurify by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ceea21602f14491be44d83de1acef48
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470870

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