Reaktion #8737

Reaktionsgleichung

DCM

(3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone

hydroxylamine hydrochloride

pyridine

→

title compound

Ausbeute 87.0%

(3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone oxime

Ausbeute 87.0%

Lösungsmittel

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheat the mixture (100° C.–105° C.) for four hours
2. 2
   SonstigeQuench the reaction mixture with water
3. 3
   Extraktionextract with ether (three times)
4. 4
   WaschenWash the ether phase with HCl (3N) and water
5. 5
   Trocknendry (MgSO4)
6. 6
   Filtrationfilter
7. 7
   Einengenconcentrate
8. 8
   Sonstigeto yield an oil
9. 9
   SonstigeRecrystallize the solid from ether

Vorschrift

Stir a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone (7 g, 0.024 mol), hydroxylamine hydrochloride (3.09 g, 0.048 mol) and pyridine (40 mL) overnight at room temperature, and then heat the mixture (100° C.–105° C.) for four hours. TLC (DCM) shows that the reaction is complete. Quench the reaction mixture with water and extract with ether (three times). Wash the ether phase with HCl (3N) and water, dry (MgSO4), filter and concentrate to yield an oil that solidifies. Recrystallize the solid from ether:hexane to obtain the title compound (6.4 g, 87% Yield), m.p. 102–103° C.

Quelle