Q64. - Organic Chemistry

Question

Question: Bupropion, sold under the trade name of Zyban, is an antidepressant that was approved to aid smoking cessation in 1997. Devise a synthesis of bupropion from benzene, organic compounds that have fewer than five carbons, and any required inorganic reagents.

Step-by-Step Solution

Answer

 Answer

Step 1: Aromatic synthesis

Many of the aromatic organic compounds can be synthesized using benzene as a starting material and treating it with specific reagents (organic or inorganic) in sequential order.

Step 2: Synthesis of bupropion

The synthesis of bupropion is shown below.

                                                Synthesis of bupropion

The first step involves the addition of the acyl group on the benzene ring (Friedel-Crafts acylation).

The chlorination of this compound results in the addition of the chlorine group at the electron-rich meta position of the ring.

The reaction of the obtained compound with bromine molecule in the presence of acetic acid leads to the substitution of bromine atom (Br) at the carbon adjacent to the carbonyl carbon.

Finally, the reaction of this compound with the amine yields bupropion.