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

HRID 2395331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395331
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-7fae9de9e87d408986b30100dba18b24
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05814646

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