Reaktion #83353

Reaktionsgleichung

2-Bromonaphthalene

4-nitrothiophenol

potassium carbonate

→

2-(4-nitrophenylthio)naphthalene

Ausbeute 12.0%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solution was filtered hot
2. 2
   Einengenconcentrated
3. 3
   workup.DISSOLUTIONdissolved in ethyl acetate
4. 4
   Waschenwashed thoroughly with 2N HCl and water
5. 5
   TrocknenThe solution was dried over sodium sulfate
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified by HPLC over silica gel
8. 8
   Wascheneluted with 5% ethyl acetate in hexane
9. 9
   SonstigeThe product was recrystallized from ethyl acetate and hexane

Vorschrift

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.

Quelle