Fluoxetine: spot the regiochemistry flaw

Single question

Final aryl ether step in the fluoxetine synthesis: the benzylic alcohol (from Mannich + reduction) is coupled with a trifluoromethylphenol. Read the substitution pattern on the phenol.

CF3 directing effects in SNAr

Para vs meta substitution on activated phenols

SAR sensitivity of fluoxetine to regiochemistry

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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