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Topic: Hypothetical grignard reagent  (Read 1705 times)

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Offline Bakterien

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Hypothetical grignard reagent
« on: June 03, 2018, 03:36:54 PM »
I wonder if its possible to make the following Grignard reagent: Br-CH2-O-CH3    +       Mg ------>  BrMg-CH2-O-CH3

Will the oxygen mess it up somehow ? Non of the protons are very acidic

If it is possible, could I use it to attack an imine ? In order to form the amine ? 

Offline rolnor

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Re: Hypothetical grignard reagent
« Reply #1 on: June 04, 2018, 05:25:20 AM »
You can make bensyloxymethyltributyltin and this can be transmetalated with butyllithium to form bensyloxymethyllithium at -78°C.
I have never seen the methoxymethylmagnesiumbromide you want to make, I think you get alpha-elimination or Wurtz-type coupling if you try to make it from methoxymethylbromide and magnesium. It was some years ago I made this chemistry so I could be remembering things wrong.

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