Quinoline → HCID 13094107, Verbindung

HRID 1156425

Reaktionsgleichung

Reaktionsgleichung von HRID 1156425
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].N1C2C(=CC=CC=2)C=CC=1>[Cu-]=O.S1C=CC=C1C([O-])=O.[Cu+2].S1C=CC=C1C([O-])=O.C(O)C.N1C=CC=CC=1>[N+:20]([C:11]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:10]=1[S:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1)([O-:22])=[O:21]

Komponenten

8

Edukt 3

HCID 7047QuinolineHCID 2401474-MercaptophenolHCID 5207064-Bromo-3-nitrobenzotrifluoride

Produkt 1

HCID 13094107HCID 13094107, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 15171005HCID 15171005, VerbindungKatalysatorHCID 178419072HCID 178419072, VerbindungKatalysator2×HCID 702EthanolLösungsmittel2×HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture containing 12.6 g (0.10 mole) of 4-mercapto phenol, 7.15 g (0.05 mole) of copper (I) oxide, and 100 ml of absolute ethanol is heated at reflux under an atmosphere of dry nitrogen until conversion to the copper thiophenate is complete, as indicated by discharge of the reddish color of the copper (I) oxide. The resultant yellow mixture is cooled to 25°, 27.0 g (0.10 mole) of 4-bromo-3-nitro-benzotrifluoride, 100 ml of quinoline, and 10 ml of pyridine are added, and the reaction vessel is equipped with a Newman still head. The reaction is now slowly heated with concomitant removal of the ethanol to 90° and maintained at this temperature until the conversion is complete, as indicated by vpc techniques. The dark liquid is cooled to 70° C., cautiously poured into 500 ml of an ice cold molar hydrochloric acid solution, and filtered, whereupon the residue is extracted with several portions of ether. The combined ether extracts are washed with a 3.0 molar hydrochloric acid solution, water until neutral, a saturated sodium chloride solution, dried (magnesium sulfate), and concentrated in vacuo to afford a quantitative yield of crude product as a dark solid. Recrystalization foam ether-hexane provides yellow crystals, mp 131°-134° of 4-(2-nitro-4-trifluoromethylphenylthio)phenol. This phenol is then reacted with 2-bromopropimate by the procedure of Example 3 above to provide the desired ethyl 2-[4-(2-nitro-4-trifluoromethylphenylthio)phenoxy] propionate, m.p. 63°-64° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureThe resultant yellow mixture is cooled to 25°
  3. customthe reaction vessel is equipped with a Newman still head
  4. temperaturemaintained at this temperature until the conversion
  5. filtrationfiltered, whereupon the residue
  6. extractionis extracted with several portions of ether
  7. washThe combined ether extracts are washed with a 3.0 molar hydrochloric acid solution, water until neutral, a saturated sodium chloride solution
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated in vacuo
  10. customto afford a quantitative yield of crude product as a dark solid
  11. customRecrystalization foam ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-d8c2e978777045e39e5510b1aa2cf845
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04335249

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