4-Bromo-2,6-dimethylpyridine

Synthesis

2,6-Dimethylpyridin-4-ol (3.25 g) in chloroform (40 mL) was treated with phosphorus pentabromide (11.5 g). The reaction mixture was heated to 60°C for 2 hours, and the solvent was removed. The residue was heated to 120°C overnight. The reaction mixture was treated with NaOH (45 g dissolved in 500 mL water), and the product was extracted into EtOAc (3 x 100 mL). The bound organic matter was dried on sodium sulfate and concentrated onto diatomaceous earth. The product, 4-bromo-2,6-dimethylpyridinium, was purified by silica gel chromatography using EtOAc in hexane (0-35%). Yellow oil, yield 2.95 g.

Figure 4: Synthetic route of 4-Bromo-2,6-dimethylpyridine

Chemical Properties

Colorless low melting solid

Uses

4-Bromo-2,6-dimethylpyridine is a reagent used in the synthesis of novel isoquinoline derivatives of potential interest for pharmaceutical, biomedical, and energy-related research.