Identify the major product X formed in the following reaction sequence: 2-Nitroanisole [ (ii) Sn/HCl ] (i) Br ₂ /FeBr ₃ Intermediate [ (iv) H ₃ PO ₂ /H ₂ O ] (iii) NaNO ₂ /HCl, 273 K X

Step-by-step solution

In 2-nitroanisole, the - OCH ₃ group is strongly activating and ortho/para directing, while the - NO ₂ group is deactivating and meta directing. Both groups synergistically direct the incoming electrophile ( Br ^+ ) to the position para to the - OCH ₃ group (position 4) as it is less sterically hindered than the ortho position. This yields 4-bromo-2-nitroanisole. Treatment with Sn/HCl reduces the - NO ₂ group to an - NH ₂ group, forming 4-bromo-2-methoxyaniline. Reaction with NaNO ₂ /HCl at 273 K converts the amine