Dimethylamine → N,N-dimethyl-5-methoxy-2-bromophenylacetamide
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:13])=[C:7]([CH2:9][C:10](Cl)=[O:11])[CH:8]=1.[CH3:14][NH:15][CH3:16]>CCOCC>[CH3:14][N:15]([CH3:16])[C:10](=[O:11])[CH2:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[Br:13]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
5-Methoxy-2-bromophenylacetyl chloride (60 g, 0.23 mol) is dissolved in anhydrous Et2O (400 mL), stirred and cooled in an ice bath. A 2 M solution of dimethylamine (228 mL, 0.46 mol) is added dropwise and the mixture allowed to warm to room temperature and stirred for 2 hours. Additional Et2O (500 mL) is added. The organic solution is washed with 1 N HCl (2×500 mL), saturated NaHCO3 (500 mL) and brine (500 mL). The organic layer is dried (Na2SO4) and concentrated by rotary evaporator. The residue is purified using flash chromatography (hexanes/EtOAc, from 7:3 to 1:9). Trituration of the crude product with Et2O/hexanes gives N,N-dimethyl-5-methoxy-2-bromophenylacetamide as a white crystalline solid (m.p. 88–90° C.).