Beilstein J. Org. Chem.2014,10, 921–928, doi:10.3762/bjoc.10.90
protocol has a broad scope for the bromination of various substituted and unsubstituted aminoanthracene-9,10-diones.
Keywords: aminoanthracene-9,10-dione; benzanthrone; KBr; nonanebis(peroxoic acid); oxidative bromination; Introduction
The brominated aminoanthracene-9,10-dione derivatives and
aminoanthracene-9,10-dione deactivate the ring towards electrophilic substitution [11]. Generally, the bromination of aminoanthracene-9,10-dione is carried out in sulfuric acid [12][13][14][15] (20 to 98%) and nitrobenzene [16][17] at a high temperature (80 to 120 °C) with or without a catalyst (like Cu or CuSO4
) [18][19][20][21]. In all processes, hazardous molecular bromine is used as a bromine source [11][12][13][14][15][16][17][18][19][20][21]. Ghaieni et. al. [22][23] have reported bromination of aminoanthracene-9,10-dione in a mixture of conc sulfuric acid with chlorobenzene, glacial acetic acid
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Graphical Abstract
Scheme 1:
Aliphatic peracid mediated bromination of aminoanthracene-9,10-dinone.