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Luis Rodriguez

2-chloro tiophene + buLi : ortho lithiation vs metal-halide exchange

Chemistry  Follow
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I dont know, I guess you gett lithiation in the 5-position. Can you use Scifinder or Reaxys? If you want to be sure you can use LDA to get pure 5-metalation. If you want metalation in the 2-position you can use magnesium and make a Grignard. Its possible you need to use excess magnesium+1,2-dichloroethane to get good Grignard.
Thanks.
No i can't :(

So is LDA  better than BuLi in tiophene orto lithiation?

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Angel Vasquez  Follow
You dont get halogen-metal exchange with LDA, you only pick the acidic 5-proton.

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Danielle Fraser  Follow
I dont know, I guess you gett lithiation in the 5-position. Can you use Scifinder or Reaxys? If you want to be sure you can use LDA to get pure 5-metalation. If you want metalation in the 2-position you can use magnesium and make a Grignard. Its possible you need to use excess magnesium+1,2-dichloroethane to get good Grignard.

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Betsy Morales  Follow
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You dont get halogen-metal exchange with LDA, you only pick the acidic 5-proton.

Thanks!!

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