Iodine → 5-Chloro-1-iodo-2-methyl-3-nitrobenzene

HRID 2299167

Reaktionsgleichung

Reaktionsgleichung von HRID 2299167
I([O-])(=O)=O.[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-:16])=[O:15])[CH:8]=1.[I:17]I.S(=O)(=O)(O)O>O>[I:17][C:11]1[CH:12]=[C:7]([Cl:6])[CH:8]=[C:9]([N+:14]([O-:16])=[O:15])[C:10]=1[CH3:13]

Komponenten

6

Edukt 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 6975Benzene, 4-chloro-1-methyl-2-nitro-HCID 23675764Sodium Iodate

Produkt 1

HCID 107564555-Chloro-1-iodo-2-methyl-3-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium iodate (158 g, 0.800 mol, 0.4 eq.) was added portionwise, under nitrogen atmosphere, to an ice-cooled mixture of 4-chloro-2-nitrotoluene (343 g, 2.00 mol), iodine (204 g, 0.800 mol, 0.4 eq.) and conc. sulfuric acid (1960 g, 20.0 mol, 10 eq.) and the resulting mixture was stirred at a temperature of 5° C. to 10° C. for 6 hours. Water (2 L) was added dropwise thereto with stirring in an ice-water bath, and the mixture was extracted with toluene (2.5 L). The combined organic layer was treated with aqueous 10% sodium thiosulfate solution, washed with water (1 L×2) and aqueous sat. sodium hydrogencarbonate solution (1 L×2) successively, dried over sodium sulfate and concentrated to give crude A-1 (548 g, purity 62%) as a yellow oil. This product was used in the following reaction without further purification.

Aufarbeitung

  1. temperaturecooled
  2. stirringwith stirring in an ice-water bath
  3. extractionthe mixture was extracted with toluene (2.5 L)
  4. additionThe combined organic layer was treated with aqueous 10% sodium thiosulfate solution
  5. washwashed with water (1 L×2) and aqueous sat. sodium hydrogencarbonate solution (1 L×2) successively
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give crude A-1 (548 g, purity 62%) as a yellow oil
  9. customThis product was used in the following reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-0a2fdcff2a6a4efa905e342e669b46d9
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495587B1

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