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Chapter 21, Problem 21.85

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QUESTION:

Aminotetralins are a class of compounds currently being studied for their promise as antidepressant drugs. The following conversion was employed during a mechanistic study associated with a synthetic route for preparing aminotetralin drugs (J. Org. Chem. 2012, 77, 55035514). Propose a three-step synthesis for this process. CH3 CO2H Three steps Br CH3 Br CH3

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QUESTION:

Aminotetralins are a class of compounds currently being studied for their promise as antidepressant drugs. The following conversion was employed during a mechanistic study associated with a synthetic route for preparing aminotetralin drugs (J. Org. Chem. 2012, 77, 55035514). Propose a three-step synthesis for this process. CH3 CO2H Three steps Br CH3 Br CH3

ANSWER:

Problem 21.85Aminotetralins are a class of compounds currently being studied for their promise asantidepressant drugs. The following conversion was employed during a mechanistic studyassociated with a synthetic route for preparing aminotetralin drugs (J. Org. Chem. 2012, 77,55035514). Propose a three-step synthesis for this process. Step-by-step solution Step 1 of 3 ^NBS (N-Bromosuccinimide) is a very good reagent for the bromination of the aromaticcompounds at the benzylic position. The first step involves bromination of the given compound.The reaction may be written as,

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