N-Iodosuccinimide → 4-Acetyl-6-chloro-3-hydroxy-2-iodobenzonitrile

HRID 626834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626834
[C:1]([C:4]1[C:11]([OH:12])=[CH:10][C:7]([C:8]#[N:9])=[C:6]([Cl:13])[CH:5]=1)(=[O:3])[CH3:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]([Cl:13])[C:7]([C:8]#[N:9])=[C:10]([I:14])[C:11]=1[OH:12])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 866975254-Acetyl-2-chloro-5-hydroxybenzonitrile

Produkt 1

HCID 866975264-Acetyl-6-chloro-3-hydroxy-2-iodobenzonitrileAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The 4-acetyl-2-chloro-5-hydroxybenzonitrile (4.9 g, 25 mmol) was dissolved in acetic acid (61.2 mL), and the N-iodosuccinimide (6.8 g, 30 mmol) was added. The reaction was heated to 80° C. and, after heating for 18 hrs, the reaction was concentrated in vacuo to remove the acetic acid. The residue was taken up in ethyl acetate, washed with sodium bicarbonate water, brine, dried over magnesium sulfate and concentrated to give a dark oil. The crude product was purified by FCC on silica gel eluting hexane:ethyl acetate gradient to give 4-acetyl-6-chloro-3-hydroxy-2-iodobenzonitrile as a yellow solid (5.3 g, 66%).

Aufarbeitung

  1. temperatureafter heating for 18 hrs
  2. concentrationthe reaction was concentrated in vacuo
  3. customto remove the acetic acid
  4. washwashed with sodium bicarbonate water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a dark oil
  8. customThe crude product was purified by FCC on silica gel
  9. washeluting hexane

Quellen und Nachweise

ORD-Eintrag
ord-b86fd382a8de4bdc8934cd5ed2c7947b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309251B2

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