Sandmeyer and Gattermann reactions
Amines and Diazonium Salts · Chemistry
Study notes
Convert aniline to m-bromonitrobenzene. Plan the sequence. Step 1: Direct bromination of nitrobenzene gives m-bromo (but we start from aniline!). Step 2: Protect: aniline → acetanilide; nitrate → p-nitroacetanilide; hydrolyze → p-nitroaniline. Step 3: Diazotize p-nitroaniline → diazonium; Sandmeyer (CuBr) → p-bromonitrobenzene. Step 4: Hmm — para, not meta! Better: diazotize aniline → Sandmeyer → bromobenzene → nitrate → m-bromonitrobenzene. Order matters!