Sodium Iodide → Methyl 5-broMo-6-iodonicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-6-chloro-3-pyridinecarboxylate (4500 mg, 17.97 mmol) in HI (30 ml) was added NaI (3501 mg, 23.36 mmol). The mixture was stirred at 50° C. overnight. Reaction was cooled at 0° C. and the precipitated solid was isolated by filtration and washed with 15 ml of MeOH. The obtained solid was suspended in 25 ml of water and pH was adjusted to 9 with NaOH 6N (1.5 ml). The aqueous phase was extracted twice with DCM and once with DCM/MeOH (5%). Organic layers were dried over Na2SO4. Volatiles were removed under vacuum to afford 2.505 g (40%) of the desired compound as a white solid. The solution of HI and MeOH was dissolved in water and pH was adjusted to 9 with NaOH 6N. The organic phase was extracted twice with DCM and once with DCM/MeOH (5%). Organic layers were dried over Na2SO4. Volatiles were removed under vacuum to afford an additional quantity of the desired compound (649 mg, 10%) as beige solid.

Provenance & Evidence