This paper reports different examples of Friedel-Crafts acylation of various substrates with dicarboxylic acid chlorides (phthalic, isophthalic, and malonyl synthons) in the presence of the AlCl3-DMF complex as catalyst. When we reacted 2(3 H)-benzothiazolone with phthalic anhydride in the presence of the AlCl3-DMF complex as catalyst, in addition to the product of 6-substitution, 4-(2-carboxybenzoyl) 2(3 H)-benzothiazolone was obtained as a contaminant. This is the first product ever obtained with a 4-substitution in the acylation of 2(3 H)-benzothiazolone.
Taverne, T., Depreux, P., Lesieur, D., Hénichart, J.-P., & Poupaert, J. (1997). AlCl3-DMF complex as catalyst in the Friedel-Craft reaction. The reactivity of anhydrides and chlorides of dicarboxylic acids. Societes Chimiques Belges. Bulletin, 106(12), 791-801. https://hdl.handle.net/2078.5/85777 (Original work published 1997)