Reaktion #551933

Reaktionsgleichung

5-chloro-3-methylbenzothiophene

N-bromosuccinimide

sodium carbonate

→

title compound

Ausbeute 88.0%

5-chlorobenzothiophene-3-carboxaldehyde

Ausbeute 88.0%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas illuminated with a 100 W lamp
2. 2
   Temperaturwhile heating
3. 3
   Temperaturat reflux temperature for 4 hours
4. 4
   Temperaturto cool
5. 5
   Filtrationthe solid was filtered off
6. 6
   Sonstigethe filtrate was evaporated to dryness
7. 7
   Sonstigeto leave a yellow oil
8. 8
   Temperaturheated under rflux, with vigorous stirring, for 5 hours
9. 9
   Temperaturto cool
10. 10
    Extraktionextracted with chloroform (3×200 ml)
11. 11
    WaschenThe organic solution was washed with brine (2×200 ml)
12. 12
    Trocknendried (MgSO4)
13. 13
    Sonstigeevaporated to dryness

Vorschrift

A stirred mixture of 5-chloro-3-methylbenzothiophene (39 g, 0.214 mole, (D22)) and recrystallized N-bromosuccinimide (77 g, 0.432 mole) in carbon tetrachloride (700 ml) was illuminated with a 100 W lamp, while heating at reflux temperature for 4 hours. The reaction mixture was allowed to cool, the solid was filtered off and the filtrate was evaporated to dryness to leave a yellow oil. This residue was treated with 10% sodium carbonate solution (450 ml) and heated under rflux, with vigorous stirring, for 5 hours. The mixture was allowed to cool and extracted with chloroform (3×200 ml). The organic solution was washed with brine (2×200 ml), dried (MgSO4) and evaporated to dryness to give the title compound as a red solid (37 g, 88%).

Quelle