o-Phenetidine → 4-Bromo-2-ethoxyaniline
Reaktionsgleichung
[Br:1]Br.[CH2:3]([O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8])[CH3:4].[OH-].[K+]>C(O)(=O)C>[Br:1][C:11]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([O:5][CH2:3][CH3:4])[CH:12]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Over approximately 1 hour, 3 ml (58.4 mmol) of bromine dissolved in 20 ml of acetic acid is added dropwise to 7.8 ml (60 mmol, 1.03 eq) of 2-ethoxyaniline diluted in 20 ml of acetic acid. When all the bromine has been added, the precipitate formed is filtered on a Buchner funnel and rinsed with acetic acid. The hydrobromide is taken up in H2O, 5 g (90 mmol, 1.5 eq) of KOH pellets is added and extracted with CH2Cl2. The organic phase is dried on MgSO4 and the solvent is evaporated. The residue is purified by column chromatography (eluent CH2Cl2/pentane 9:1) to produce 7.52 g of the expected product as a brown oil (yield: 58%).