Iodine → 2,5-Dichloro-3-iodobenzoic acid

HRID 274837

Reaktionsgleichung

Reaktionsgleichung von HRID 274837
[I:1]I.N(OC(C)(C)C)=O.N[C:11]1[C:12]([Cl:21])=[C:13]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[C:14]([OH:16])=[O:15].N(OCCCC)=O>CS(C)=O.O>[Cl:21][C:12]1[C:11]([I:1])=[CH:19][C:18]([Cl:20])=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Komponenten

7

Edukt 4

HCID 807Iodine2×HCID 8630ChlorambenHCID 10906Tert-Butyl nitriteHCID 10996Butyl nitrite

Produkt 1

HCID 214781212,5-Dichloro-3-iodobenzoic acidAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

In a flask 48.35 grams (0.191 mole) of iodine was dissolved in 90 mL of dimethyl sulfoxide. To this solution was added 29.47 grams (0.286 mole) of tertiary butyl nitrite. A solution of 39.25 grams (0.191 mole) of 3-amino-2,5-dichlorobenzoic acid in 130 mL of dimethyl sulfoxide was added dropwise to the solution of iodine and butyl nitrite. During this addition the temperature rose from 20° C. to 50° C., at which temperature the addition was stopped until the reaction mixture had cooled to 35° C. The addition was then completed. When the addition was complete, the reaction mixture was stirred for approximately 16 hours, then poured into water, and this mixture was extracted with ethyl acetate. The extracts were combined and washed with an aqueous solution of sodium hydrogen sulfate and finally with water. The combined extracts were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, yielding 51.34 grams of 2,5-dichloro-3-iodobenzoic acid as a solid.

Aufarbeitung

  1. additionDuring this addition the temperature
  2. customrose from 20° C. to 50° C., at which temperature
  3. additionthe addition
  4. additionThe addition
  5. additionWhen the addition
  6. extractionthis mixture was extracted with ethyl acetate
  7. washwashed with an aqueous solution of sodium hydrogen sulfate and finally with water
  8. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customThe solvent was evaporated from the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-001cbe39c22a432dafc83796b36bb5c4
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391541

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