Question
Asked Jun 20, 2019
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Please devise synthesis of the product compounds below from their respective starting material. 

NH
Br
18
H0
HO
Albuterot-(forasthma)
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NH Br 18 H0 HO Albuterot-(forasthma)

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Expert Answer

Step 1

Oxirane reacts with tertiary butyl amine to form an alcohol substituted product. On oxidation, with CrO3 it will be converted into carboxylic acid which on further treatment with SOCl2 gives acyl chloride. The series of steps involved are shown below.

On
1
CO
11
-NH-C-CH2
NH-CH-C-OH
0
-NK-CH -
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On 1 CO 11 -NH-C-CH2 NH-CH-C-OH 0 -NK-CH -

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Step 2

The bromo group of benzene substituted reactant reacts with KNH2 to form amine which on further treatment with HNO2 and HCl gives aryl diazonium salts. Aryl diazonium salt on reaction with H3PO2 leads to the removal of diazonium group from the compound.

Bи
K NH2
-NH
Им0z,
иd,
А
и, Р0
.а
с
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Bи K NH2 -NH Им0z, иd, А и, Р0 .а с

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Step 3

In the last step, the products formed in first and second steps undergo Friedel craft acylation reaction in the presence of AlCl3 and leads to the substitution of acyl gro...

+ d-c-C-NH.
Alds
NH
NH.
Atid
NH
NH
Aud
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+ d-c-C-NH. Alds NH NH. Atid NH NH Aud

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