Nitration of three regioisomers of bromo-fluorobenzaldehyde proceeds regioselectively, notably with H₂SO₄/HNO₃ at 0 °C. The thereby synthesized tetrasubstituted aromatics, endowed with orthogonal substituents, can be elaborated via Pd-catalysed coupling, reduction and reductive amination reactions. As a test-case, these compounds were converted into EGFR inhibitors related to Gefitinib, whose activity was rationalised by docking studies.