Tert-Butyl hypochlorite → 2-Amino-5-chloro-4-fluorobenzoic acid

HRID 10318

Reaktionsgleichung

Reaktionsgleichung von HRID 10318
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[Cl:12]OC(C)(C)C>C(Cl)Cl.C(O)(=O)C>[Cl:12][C:10]1[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]([NH2:11])=[CH:3][C:2]=1[F:1]

Komponenten

5

Edukt 2

HCID 521297Tert-Butyl hypochloriteHCID 27249674-Fluoroanthranilic acid

Produkt 1

HCID 219792552-Amino-5-chloro-4-fluorobenzoic acidAusbeute 111,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-fluoroanthranilic acid (0.882 g, 5.69 mmol) in methylene chloride (50 ML) and acetic acid (10 mL) is added tert-butyl hypochlorite (0.71 mL, 6.25 mmol) solution in dichloromethane (1 mL) dropwise over 1 minute. After 90 minutes, the reaction mixture is washed with water and brine. The organic layer is dried over MgSO4, filtered, and the filtrate concentrated to afford 5-chloro-4-fluoroanthranilic acid (1.20 g). MS CI: m/e 188 (M+).

Aufarbeitung

  1. washthe reaction mixture is washed with water and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated

Quellen und Nachweise

ORD-Eintrag
ord-fa7df086e4e6499c96d448bcfa269c2e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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