Isoamyl Nitrite → Dimethyl 2,6-dichloroterephthalate

HRID 449895

Reaktionsgleichung

Reaktionsgleichung von HRID 449895
N[C:2]1[C:11]([Cl:12])=[C:10]([C:13]([O:15][CH3:16])=[O:14])[C:9]([Cl:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(ON=O)CC(C)C>C1COCC1>[Cl:12][C:11]1[CH:2]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=[C:9]([Cl:17])[C:10]=1[C:13]([O:15][CH3:16])=[O:14]

Komponenten

4

Edukt 2

HCID 8053Isoamyl NitriteHCID 20714731Dimethyl 2-amino-3,5-dichloroterephthalate

Produkt 1

HCID 7730227Dimethyl 2,6-dichloroterephthalateAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of dimethyl 2-amino-3,5-dichloroterephthalate (200 g, 0.72 mol) in THF (1 L) at room temperature was slowly added isoamylnitrite (240 mL). The mixture was heated under reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with petroleum-diethyl:ether (50:1) to give dimethyl 2,6-dichloroterephthalate (187 g, yield: 98%) as a light yellow solid.

Aufarbeitung

  1. customat room temperature
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with petroleum-diethyl:ether (50:1)

Quellen und Nachweise

ORD-Eintrag
ord-ea54b14529e34b05be5d2e838c3a9823
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486950B2

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