Hi y'all! I was hoping someone could explain a mechanism for this reaction and perhaps explain what I did wrong.
For my mechanism I did the following:
- Combine trifluoromethanesulfonic anhydride (Tf2O) with phenol --> benzene with attached OTf
-to make the alcohol a good leaving group
- Combine 1-pentyne with 1 equivalent of HBr and peroxides --> 1-bromo-1-pentene
-to set it up for Fiedel-Crafts alkylation and make it a double bound like it is in the desired product
- Combine products of 1 and 2 --> 1-phenyl-1-pentene
-to replace OTf with the O-P directing alkyl chain
- Combine t-butanol and HCl --> chlorine replaces OH
-to get good leaving group for FC-type reaction
- Combine products from 4 and 5 --> Compound A
-Fiedel Crafts alkylation again added to P and O positions (mixture but directions didn't say it had to be pure)
Could you please explain what my proposed mechanism would actually result in and what a good mechanism for this synthesis would be? Thanks in advance!