Friday, 22 April 2016

organic chemistry - How to develop a retrosynthesis plan for 2-[(E)-2-(3-bromophenyl)ethenyl]-1,3-benzoxazole?



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.


2-[(E)-2-(3-bromophenyl)ethenyl]-1,3-benzoxazole


How would I go about doing this?



Answer



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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