Hydrochloric Acid → 3-Amino-5-bromobenzonitrile
Reaktionsgleichung
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1)[C:5]#[N:6].[Sn].Cl>CO>[NH2:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Br:1])[CH:9]=1)[C:5]#[N:6]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of 3-bromo-5-nitrobenzonitrile (1 g, 4.4 mmol) in MeOH (50 mL) was added tin (5.23 g, 44 mmol) and 3N HCl (44 mL, 132 mmol). The reaction mixture was stirred at RT for 2 h, the filtered off and washed with MeOH. The filtrate was concentrated in vacuo, and the remaining water phase was basified to pH=12 by addition of 4N NaOH. The aqueous layer was extracted twice with EtOAc (100 mL), the combined organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a yellowish solid. MS (LC/MS): 197.0 [M+H]+; tR (HPLC conditions c): 4.30 min.