3-Chloro-4-fluoroaniline → 5-Chloro-4-fluoro-2-iodobenzenamine

HRID 555707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555707
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C1C(=O)N([I:17])C(=O)C1>CC(O)=O>[Cl:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([I:17])=[C:4]([CH:3]=1)[NH2:5]

Komponenten

4

Edukt 2

HCID 97083-Chloro-4-fluoroanilineHCID 120273N-Iodosuccinimide

Produkt 1

HCID 247872515-Chloro-4-fluoro-2-iodobenzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 3-chloro-4-fluoroaniline (12.9 g, 88.9 mmol) and NIS (22.0 g, 97.8 mmol) in AcOH (90 mL) is stirred at RT for 1.5 h. After completion, the reaction mixture is quenched by H2O, DCM is added and the organic layer is washed with brine, dried over MgSO4 and evaporated in vacuo. Silica gel flash chromatography of the residue affords 5-chloro-4-fluoro-2-iodoaniline as a colorless powder; HPLC: AtRet=4.75 min; 1HNMR (CDCl3) 7.40 (d, 1H), 6.75 (d, 1H), 4.00 (bs, 2H).

Aufarbeitung

  1. customAfter completion, the reaction mixture is quenched by H2O, DCM
  2. additionis added
  3. washthe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5bc46730a06344e6ad58a1f150ea8a56
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053457B2

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