Reaktion #454044

Reaktionsgleichung

1-bromo-4-nitrobenzene

2-(tributylstannyl) 3,4-(ethylenedioxy)thiophene

→

1-(3,4-ethylenedioxythien-2-yl)-4-nitrobenzene

Ausbeute 68.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   Temperaturthe mixture was refluxed for a total of 20 h
3. 3
   TemperaturAfter cooling
4. 4
   Filtrationthe mixture was filtered
5. 5
   Sonstigethe solvent was evaporated
6. 6
   Sonstigeto afford a solid
7. 7
   FiltrationFiltration

Vorschrift

To a refluxing solution of 1-bromo-4-nitrobenzene (2.762 g, 13.67 mmol) in toluene (250 mL) was added tetrakis(triphenylphosphine)palladium(0) (75 mg). After 20 min, 2-(tributylstannyl) 3,4-(ethylenedioxy)thiophene (6.05 g, 14.03 mmol) was added via a syringe. After complete addition, the mixture was refluxed for a total of 20 h. After cooling, the mixture was filtered and the solvent was evaporated to afford a solid. Filtration using hot hexane gave 1-(3,4-ethylenedioxythien-2-yl)-4-nitrobenzene, 2.46 g, yield=68%, mp=184-186° C. IR (KBr; in cm-1) 3066, 2946, 1592, 1506, 1477, 1338, 1066 and 851. 1H NMR (CDCl3 ; δ in ppm): 4.285 (m, 2H), 4.376 (m, 2H), 6.468 (s, 1H), 7.852 (d, J=9.9 Hz, 2H) and 8.197 (d, J=9.9 Hz, 2H). 13C NMR (CDCl3 ; δ in ppm): 64.25, 64.94, 100.93, 115.10, 124.03, 125.61, 139.72, 140.53, 142.43 and 145.37. MS(EI) m/z (rel int): 263 [(M)+, 27%], 233 [(M+ --NO), 8%] and 166[(M+ --C5H5O2), 9%]. Anal. Calcd for C12H9NO4S: C, 54.75; H, 3.45;, N, 5.32; S, 12.18. Found: C, 55.04; H, 2.99; N, 4.05; S, 11.57.

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