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I need to retro-synthetically design a valid synthesis plan (in 2 steps, from cheap starting materials available over at Sigma Aldrich) for a target compound, pictured below.

enter image description here

How would I go about doing this?

*edit A follow up question regarding another synthesis strategy that I found myself in the comment below.

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Extempore, this should be available by the reaction of 3-bromocinnamaldehyde with 2-aminophenol. Samarium triflate as a catalyst might be a good idea.

retrosynthesis of benzoxazole

In any case, I'd start the retrosynthesis at the benzoxazole moiety.

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  • $\begingroup$ Thank you very much! In the meantime I tried to develop another strategy as well, I've done some research and found another way to synthesize this via reaxys. If I may, I do have a follow up question regarding this: would this reaction go the same way if I were to react the benzoxazole without the halogen (F)? If not, is there a way to remove it from the target molecule? Here's a link to the !synthesis plan. Once again, thank you very much for the assistance. $\endgroup$ – monozuki Oct 31 '16 at 21:22
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How about a more classic Wittig reaction between 3-Bromobenzaldehyde and 2-(chloromethyl)-1,3-benzoxazole?

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