Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex was successfully used as a new reagent for the synthesis of carboxylic acid bromides which were isolated as individual substances or were identified by conversion into the corresponding anilides. The reaction is chemoselective, and it can be applied to polyfunctional compounds, e.g., hydroxy acids.
Scheme 1.
IIRCOBr + Ph 3 PO RCOOH + Ph 3 P + O Br Br Br Br I [RCOOPPh 3 ] Br + OH Br Br Br III II
2005Carboxylic amides Q 0490Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone Complex as a Reagent for Preparation of Carboxylic Acid Bromides. -It is noteworthy that this methodology for the preparation of acid bromides is chemoselective, and it can be applied to polyfunctional compounds such as hydroxy acids. The bromides are identified by conversion to the corresponding anilides (III). -(MATVEEVA, E. D.; PODRUGINA, T. A.; SANDAKOVA, N. G.; ZEFIROV, N. S.; Russ.
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