Conjugate addition of RMgX to nitroarenes. A very useful method of alkylation of aromatic nitro compounds was written by Bartoli, Giuseppe;Bosco, Marcella;Baccolini, Graziano. And the article was included in Journal of Organic Chemistry in 1980.Quality Control of 3-Methyl-4-nitroanisole This article mentions the following:
Alkylation of mononitroarenes involves treatment of 1 mol nitro compound with 2 mol RMgX at 0° for a few min to give o– or p-alkylnitronate adducts, which are immediately converted in situ to aromatic alkylnitro derivatives by adding 0.66 mol KMnO4 in Me2CO-H2O. The wide applicability of this method is substantiated by good yields obtained for a large number of mono- and bicyclic systems. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Quality Control of 3-Methyl-4-nitroanisole).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Quality Control of 3-Methyl-4-nitroanisole
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem