Acetic Acid → 3-Chloro-4,5-difluoroanthranilic acid

HRID 10317

Reaktionsgleichung

Reaktionsgleichung von HRID 10317
[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:9][C:10]=1[F:11])[C:6]([OH:8])=[O:7].C(O)(=O)C.C(O[Cl:22])(C)(C)C>ClCCl.C(OCC)(=O)C>[Cl:22][C:3]1[C:2]([F:1])=[C:10]([F:11])[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH2:12]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 521297Tert-Butyl hypochloriteHCID 7359652-Amino-4,5-difluorobenzoic acid

Produkt 1

HCID 219789243-Chloro-4,5-difluoroanthranilic acidAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4,5-difluoroanthranilic acid (2.45 g, 14.2 mmol) in dichloromethane (25 mL) is added acetic acid (10 mL) and hypochlorous acid tert-butyl ester (1.75 mL, 15.6 mmol). After 2 hours, the reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic layer is dried over MgSO4, filtered, and concentrated. The resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane) to afford 3-chloro-4,5-difluoroanthranilic acid as an oil (2.97 g). MS CI: m/z 206 (M+).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cce603932cca4abba7de902112a6eb98
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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