Hello all, For a project I am working on, it would be convenient to be able to make the following Grignard reagent: N-Methyl indole-6-Magnesium Bromide (or Chloride). A search of STNeasy failed to turn up such a compound, but with the N- blocked by the Methyl, it seems to me that the Bromine should be reactive enough to make the Grignard. According to the literature, the N-Methyl-6-Lithio compound can be made by reaction with t-Butyllithium. I could use the lithio-derivative, but for a number of reasons, the Grinard would be more convenient. I would be most grateful for anyone's thoughts on the matter. Get some of the bromide and try it and see.  It'll take you less time to try the reaction than to ask for advice on a questionable public forum like sci.chem. However, if you want my opinion, it'll work.  If you buy the bromide and can't make the Grignard, you'll have to resort to the lithium reagent anyway, so you won't waste the bromide. Why will the Grignard be more convenient?  In my experience, lithium reagents are far more convenient.  You don't have to use t-BuLi, you should get quantitative yield with n-BuLi in ether (preferrable for workup, and stable to r.t. n-BuLi) or THF (less convenient for workup, and slowly munched by r.t. n-BuLi).  With Grignard reagents, if the formation reaction is sluggish, you gotta worry about it initiating smoothly (as opposed to initiating after you've added half of the bromide

Hello all, For a project I am working on, it would be convenient to be able to make the following Grignard reagent: N-Methyl indole-6-Magnesium Bromide (or Chloride). A search of STNeasy failed to turn up such a compound, but with the N- blocked by the Methyl, it seems to me that the Bromine should be reactive enough to make the Grignard. According to the literature, the N-Methyl-6-Lithio compound can be made by reaction with t-Butyllithium. I could use the lithio-derivative, but for a number of reasons, the Grinard would be more convenient. I would be most grateful for anyone's thoughts on the matter. If SOP is DOA even with flamed glassware... Do the Grignard in strictly dry and oxygen-free THF (distilled under inert gas from royal purple benzophenone sodium).  If it won't go after the usual pushing and crushing, try adding two equivalents of TMEDA freshly run down an Activity Zero basic alumina column (like a 9 dispo-pipette with a little wad of oven-dried glass wool at the bottom, the alumina, a septum at the top, and open syringe drip through some clean TMEDA.  You'll be surprised at what collects at the top of the alumina).  TMEDA should be inert toward the aromatic halide. A fellow I know takes a piece of thin copper wire freshly cleaned in HNO3, washed and dried, tightly wraps a bight about a magnesium shaving (latex gloves), and drops that in as an electrochemical kick.  It may be a totem. If the lithio compound exists, the Grignard should be doable.