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


How would I go about doing this?


2 Answers 2


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.

  • $\begingroup$ 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, 2016 at 21:22

How about a more classic Wittig reaction between 3-Bromobenzaldehyde and 2-(chloromethyl)-1,3-benzoxazole?


Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.