Iodine → 3-Iodo-5-nitrobenzoic acid

HRID 77739

Reaktionsgleichung

Reaktionsgleichung von HRID 77739
[I:1]I.[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10])([O-:5])=[O:4]>S(=O)(=O)(O)O>[I:1][C:13]1[CH:12]=[C:8]([CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=1)[C:9]([OH:11])=[O:10]

Komponenten

4

Edukt 2

HCID 807IodineHCID 84973-Nitrobenzoic acid

Produkt 1

HCID 805803-Iodo-5-nitrobenzoic acidAusbeute 97.987,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of iodine (137.95 g, 0.5436 mmol) in fuming sulfuric acid (250 ml) was added m-nitrobenzoic acid (64.6 g, 0.3866 mmol) at room temperature. The reaction mixture was slowly heated to 85° C. overs 2 hours and stirred at the same temperature for another 12 hours. The reaction mixture was cooled to room temperature and poured into ice, and the aqueous solution was extracted with dichloromethane. The organic phase was separated and washed with water, 2.0 M solution of Na2S2O3 and brine, and then dried over Na2SO4. Solvent was removed under reduced pressure to yield 3-iodo-5-nitrobenzoic acid as slight yellow solid 111 g, yield 98%. MS (M+H)=294.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured into ice
  3. extractionthe aqueous solution was extracted with dichloromethane
  4. customThe organic phase was separated
  5. washwashed with water, 2.0 M solution of Na2S2O3 and brine
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b97850d313f4c7b84b4152af8b9bd7b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841336B2

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