Grignard Reaction

Our assignment for this week's blog was to find an experiment carried out involving the grignard reaction, organolithium, or organocuprate reactions in at least one synthetic step. The Grignard reaction is an important tool in the formation of carbon-carbon bonds and for the formation of carbon-phosphorus, carbin-tin, carbon-silicon, carbon-boron, and other carbon-heteroatom bonds. This type of reaction acts as nucleophiles and attack electrophilic carbon atoms that are present within polar bonds, carbonyl groups for example, to yield a new carbon-carbon bond. The reaction I found involved the formation of 4-Nonylbenzoic acid. Below is the overall reaction of the experiment.

In this experiment, the grignard reaction takes place in part A. The nonylmagnesium bromide/Fe(acac)3 catalyst then THF for 7 min in 0 degrees celsius, replaces the Chloro group on the benzene ring with the 9 carbon chain, nonyl group. The IUPAC name of this product in A is 4-nonylbenzoic acid methyl ester. Expensive noble metal catalysts were replaced in this experiment by cheap, air stable, commercially available and toxicology benign iron salts without any loss in efficiency, using inexpensive Grignard reagents as the preferred coupling partners. "When applied to polyfunctional substrates, iron catalyzed reactions allow either for selective, exhaustive, or consecutive cross-coupling processes to be carried out in "one pot." (1)




Reference:
1. Furstner, Leitner, and Seidel. 4-Nonylbenzoic Acid. Organic Syntheses, Vol. 81, p. 33 (2005); Coll. Vol. 11, p.353 (2009)