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I was solving some reactivity problems, and I was asked to prepare toluene from bromobenzene.

While the suggested solution of the problem involves the preparation of a Grignard reagent, followed by a reaction with methyl bromide, I was wondering:

Could the same compound be prepared with the straightforward reaction between bromobenzene and methyl lithium?

I tried to search some similar reactions, but I found nothing for both the possible ways.

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  • $\begingroup$ Probably not, bromobenzene might not be electrophilic enough. $\endgroup$ – Martin - マーチン Apr 26 '17 at 5:48
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MeLi certainly does lithium-halogen exchange and in the presence of MeI takes bromobenzenes to toluenes Synth. Comm. 2001 2323

If you're asking whether the MeBr produced by the exchange can act as the methylating agent? I have never seen this reported but maybe someone else can pull up a reference.

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