Potassium Iodide → 2-Chloro-6-iodobenzoic acid

HRID 508773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 508773
N[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].N([O-])=O.[Na+].[I-:16].[K+]>Cl.O.S(=O)(=O)(O)O>[Cl:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:2]([I:16])[C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

7

Edukt 3

HCID 4875Potassium IodideHCID 750712-Amino-6-chlorobenzoic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 133993742-Chloro-6-iodobenzoic acidAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To the cold solution of 2-amino-6-chlorobenzoic acid (2.0 g, 11.6 mmol) in conc. HCl (10 mL) was added aq. solution of sodium nitrite (0.8 g, 11.6 mmol) at 0° C. followed by addition of solution of potassium iodide (2.88 g, 17.4 mmol) in water and conc. sulphuric acid (1 mL). The reaction mixture was refluxed for 2 h. The reaction mass was washed with sodium metabisulphate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 2.0 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 7.08 (t, J=7.8 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 8.37 (br s, 1H); MS (m/z): 280.59 (M)−.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. washThe reaction mass was washed with sodium metabisulphate solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-63c9f4e59ba6430b9c4820a7851bbee4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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