Sodium Sulfite → 2,4-Difluoro-5-iodobenzoic acid

HRID 875058

Reaktionsgleichung

Reaktionsgleichung von HRID 875058
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 3

HCID 24437Sodium SulfiteHCID 741022,4-Difluorobenzoic acidHCID 120273N-Iodosuccinimide

Produkt 1

HCID 111297952,4-Difluoro-5-iodobenzoic acidAusbeute 215,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

2,4-Difluorobenzoic acid (100 g, 633 mmol) was dissolved in concentrated sulfuric acid (400 ml), and N-iodosuccinimide (142 g, 601 mol) was added by portions at not more than 5° C. After the completion of the addition, the mixture was stirred at the same temperature for 6 hr. The reaction mixture was poured into ice water (ca. 2400 ml), then saturated aqueous sodium sulfite solution was added, and the mixture was stirred. The precipitated solid was collected by filtration, washed with water, and vacuum dried to give crude crystals (188 g). The crude crystals obtained in the same manner were combined (total amount 568 g), and recrystallized from 50% aqueous ethanol (2600 ml) to give 2,4-difluoro-5-iodobenzoic acid (388 g, yield 68%) as a white solid.

Aufarbeitung

  1. additionAfter the completion of the addition
  2. stirringthe mixture was stirred
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water, and vacuum
  5. customdried
  6. customto give crude crystals (188 g)
  7. customThe crude crystals obtained in the same manner
  8. customrecrystallized from 50% aqueous ethanol (2600 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7bb6b9e603e741d797d6709ccdc6d2bb
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981103B2

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