153929-32-9Relevant academic research and scientific papers
Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides
Quesnel, Jeffrey S.,Kayser, Laure V.,Fabrikant, Alexander,Arndtsen, Bruce A.
supporting information, p. 9550 - 9555 (2015/06/30)
We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products. The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri-tert-butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon-halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.
Easy and General Method for the Preparation of m- and p-Acylbenzoic Acids: A New Synthesis of rac-Suprofen
Camps, Pelayo,Gimenez, Silvia,Farres, Xavier,Mauleon, David,Carganico, Germano
, p. 641 - 644 (2007/10/02)
A method for the preparation of m- and p-acylbenzoic acids 3 based on the Claisen condensation of isophthalic or terephthalic diesters 1 with α-methylenecarboxylic esters 2 is described. p-Propionylbenzoic acid p-4 (R=Me) is used in a new synthesis of rac-suprofen (11). Key Words: Acylbenzoic acids / Claisen condensation / rac-Suprofen / Thalium(III) nitrate
