Is it possible to form a Grignard reagent from 1-chloro-3-nitrobenzene, as shown below?
Specifically, will the nitro group react with the Grignard reagent formed?
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8$\begingroup$ No. Aromatic nitro groups react with grignards - see Bartoli reaction. $\endgroup$– WaylanderJul 30, 2018 at 12:41
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$\begingroup$ An organozinc would probably work $\endgroup$– orthocresolJul 30, 2018 at 13:29
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$\begingroup$ It really depends on what you're trying to accomplish with your organometallic reagent. $\endgroup$– ZheJul 30, 2018 at 18:23
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1 Answer
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Aromatic nitro groups are not compatible with Grignards as they react with the nitro group. An example of this being useful is the Bartoli synthesis of indoles from vinyl Grignards (Tet. Letts. 1989, 30 2129, Curr. Org. Chem.. 2005, 9, 163). The first step of the Bartoli is addition of the vinyl Grignard to the O of the N=O of the nitro group so I presume this would be true for other Grignards and is the reason for the incompatibility.
answered Jul 30, 2018 at 19:45