Iodine → Ethyl 4-amino-2-chloro-5-iodobenzoate

HRID 514242

Reaktionsgleichung

Reaktionsgleichung von HRID 514242
[I:1]I.[NH2:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:15])[CH:5]=1>C(O)C.S([O-])([O-])(=O)=O.[Ag+].[Ag+]>[NH2:3][C:4]1[C:14]([I:1])=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([Cl:15])[CH:5]=1

Komponenten

5

Edukt 2

HCID 807IodineHCID 13287887Ethyl 4-amino-2-chlorobenzoate

Produkt 1

HCID 58247958Ethyl 4-amino-2-chloro-5-iodobenzoateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 159865Silver sulfateKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

An iodine solution in ethanol was admixed with silver(I) sulphate and ethyl 4-amino-2-chlorobenzoate and then stirred at room temperature for 45 min. The reaction mixture was filtered through a frit and the filtrate was concentrated under reduced pressure. The residue was slurried in EtOAc, and dilute sodium hydrogencarbonate solution was added. Once everything had gone into solution, the aqueous phase was removed and sodium thiosulphate was dissolved therein. The organic phase was washed again with the aqueous phase and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated under reduced pressure. Column chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate) gave 1.85 g (74% of theory) of ethyl 4-amino-2-chloro-5-iodobenzoate.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a frit
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additiondilute sodium hydrogencarbonate solution was added
  4. customthe aqueous phase was removed
  5. dissolutionsodium thiosulphate was dissolved
  6. washThe organic phase was washed again with the aqueous phase
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. dry with materialThe combined organic phases were dried over sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customColumn chromatography purification on silica gel with cyclohexane/ethyl acetate as the eluent (gradient from 10% ethyl acetate to 33% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9cba2ea5e6944709ba4f889e37ea1d3c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09107411B2

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