Question #44934

Compound $\mathbf{A}$ ($\ce{C9H10Br2}$) is treated with 1 equivalent of potassium phthalimide in DMF at $350\text{ K}$, followed by heating with aqueous $\ce{NaOH}$ to yield compound $\mathbf{B}$ ($\ce{C9H12BrN}$). Compound $\mathbf{B}$ is then treated with $\ce{NaNO2}$ and $\ce{HCl}$ at $273\text{ K}$, followed by the addition of phenol in dilute $\ce{NaOH}$. No azo dye is formed; instead, a clear solution with the evolution of a colorless gas is observed, yielding compound $\mathbf{C}$ ($\ce{C9H11BrO}$) as the major organic product. Compound $\mathbf{C}$ on vigorous oxidation with acidic $\ce{KMnO4}$ yields a monobasic acid $\mathbf{D}$ ($\ce{C7H5BrO2}$). Identify the correct structure of starting material $\mathbf{A}$.