Chlorosuccinimide → Ethyl 5-(4-tert-butylphenyl)-4-chloroisoxazole-3-carboxylate
Reaktionsgleichung
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:12]=2[Cl:21])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of ethyl 5-(4-tert-butylphenyl)isoxazole-3-carboxylate (2.0 g, 7.32 mmol) and N-chlorosuccinimide (2.44 g, 18.3 mmol) in acetic acid (50 mL) was heated to reflux for 3 days. The reaction mixture was then allowed to cool to room temperature, poured over ice and the resulting white solid was collected, dissolved in ethyl acetate and the organics washed with water, brine and dried with sodium sulphate before being filtered, and evaporated in vacuo. The resultant residue was re-dissolved in dichloromethane, this was then extracted with sodium carbonate solution, and dried using a hydrophobic frit. The organics were removed in vacuo to obtain ethyl 5-(4-tert-butylphenyl)-4-chloroisoxazole-3-carboxylate (0.81 g, 2.63 mmol).