Table 1. General Pathway for the Synthesis of Bromo Mono-Substituted Compounds^b.

^a(A) Methyl 3-bromo-4-hydroxybenzoate, K₂CO₃, DMF, rt, overnight (45% for 2e); (B) amine component R₃, DBU (25% for 2f).

^bReagents and conditions: (A) substituted 4-hydroxybenzaldehde, K₂CO₃, DMF, rt, overnight (43% for 2a, 39% for 2b, 38% for 2c, and 52% for 2d); (B) amine component, NaBH₃CN, AcOH, DMF, rt, overnight (53% for 2g, 65% for 2h, 56% for 2i, 72% for 2j, and 51% for 2k).