Hydrochloric Acid → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 14291

Reaktionsgleichung

Reaktionsgleichung von HRID 14291
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl.N([O-])=O.[Na+].[I-:20].[K+]>O>[I:20][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acidAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Versuchsvorschrift

To an ice-cold, stirred solution of 3-amino-5-(methoxycarbonyl)benzoic acid (5.19 g, 26.59 mmol) in a 2 N hydrochloric acid (156 mL) was added a solution of sodium nitrite (1.84 g, 26.67 mmol) in water (10.8 mL). This mixture was then added dropwise to an ice-cold, stirred solution of potassium iodide (8.84 g, 53.25 mmol) in water (26.2 mL). After stirring for 35 min, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride, dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid) afforded 3-iodo-5-(methoxycarbonyl)benzoic acid (4.48 g): 1H NMR (500 MHz, DMSO-d6): δ 13.49 (br s, 1H), 8.45-8.38 (m, 3H), 3.83 (s, 3H); ESI-MS (m/z): 305 [M+H]+.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-b9e365e738df4d5f94ed7d7af91e7e2d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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