2-Bromonaphthalene → 2-(4-Nitrophenylthio)naphthalene

HRID 55075

Reaktionsgleichung

Reaktionsgleichung von HRID 55075
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1.[Cu]>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]

Komponenten

6

Edukt 3

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 158094-Nitrobenzenethiol

Produkt 1

HCID 189716852-(4-Nitrophenylthio)naphthaleneAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-Bromonaphthalene (0.08 moles, 16.6 g), 4-nitrothiophenol (0.08 moles, 12.4 g), potassium carbonate (0.1 moles, 13.4 g), copper bronze (6.0 g) and cuprous chloride (0.02 moles, 2.0 g) were heated under reflux for 4 days in 300 ml pyridine. The solution was filtered hot, concentrated, dissolved in ethyl acetate and washed thoroughly with 2N HCl and water. The solution was dried over sodium sulfate, concentrated and purified by HPLC over silica gel eluted with 5% ethyl acetate in hexane. The product was recrystallized from ethyl acetate and hexane to yield 2-(4-nitrophenylthio)naphthalene 2.6 g, 12% in the first crop. Mass spec. (FD) 281.

Aufarbeitung

  1. filtrationThe solution was filtered hot
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate
  4. washwashed thoroughly with 2N HCl and water
  5. dry with materialThe solution was dried over sodium sulfate
  6. concentrationconcentrated
  7. custompurified by HPLC over silica gel
  8. washeluted with 5% ethyl acetate in hexane
  9. customThe product was recrystallized from ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-09578c9c56544be3ba3e104ce53517cd
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624937

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