O-Phenylenediamine → 2,3-Bis(bromomethyl)quinoxaline
Reaktionsgleichung
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Br:9][CH2:10][C:11](=O)[C:12](=O)[CH2:13][Br:14]>C1C=CC=CC=1>[Br:9][CH2:10][C:11]1[C:12]([CH2:13][Br:14])=[N:8][C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:7]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 1,2-phenylenediamine (0.1 mole, 10.8 g) and 1,4-dibromo-2,3-butanedione (0.1 mole, 24.4 g) was refluxed in benzene (200 mL) using a Dean-Stark trap for one hour. The reaction mixture was then evaporated to dryness in vacuo and the residue flash chromatographed on silica gel (15:1). Elution with 15% hexane/chloroform afforded 29.38 g of 2,3-bis(bromomethyl)quinoxaline, m.p. 150°-151° C.; 1H NMR (CDCl3, 200 MHz): δ4.92 (s, 4H, CH2), 7.8 (m, 2H, ArH), 8.05 (m, 2H, ArH).