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• Synthesis

  At 0°C, a small solution of 7.4 g (107 mmol) sodium nitrate in 15 mL of distilled water was added to a solution of 10.0 g (65.3 mmol) 3,5-dimethoxyaniline in 30 mL of 48% hydrobromic acid until the presence of the diazonium salt was observed with starch-potassium iodide paper. Simultaneously, a mixture of 5.2 g (36 mmol) cuprous bromide in 5.2 mL of 48% hydrobromic acid was heated to boiling in another flask. The resulting diazonium salt solution was added in small amounts to the cuprous bromide-hydrobromic acid solution, maintaining its boiling point. After the addition was complete, the total reaction mixture was stirred and heated for another 30 minutes. The resulting crude product was purified by steam distillation, yielding 7.84 g of 1-bromo-3,5-dimethoxybenzene as a white solid, in a yield of 55.8%, with a melting point of 63-64°C.

  

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