2,5-Dibromopyridine

Chemical properties

2,5-Dibromopyridine is an off-white crystalline solid. It is insoluble in water but soluble in strong polar organic solvents. It exhibits strong alkalinity.

The Uses of 2,5-Dibromopyridine

2,5-Dibromopyridine (cas# 624-28-2) is a compound useful in organic synthesis.

What are the applications of Application

2,5-Dibromopyridine is used for:
(1) Preparation of Lenacapavir for the treatment of HIV patients.
(2) Synthesis of 2,5-disubstituted pyridine liquid crystals. Fifteen 2,5-disubstituted pyridine liquid crystals were synthesised under Negishi-coupled conditions using different reactivities of the bromine atom in 2,5-dibromopyridine.
(3) Carboalkoxylation of 2,5-dibromopyridine with carbon monoxide and an alcohol in the presence of palladium acetate and 1,1′-bis(diphenylphosphino) ferrocene (dppf) occurs regiospecifically to afford esters of 5-bromo-pyridine-2-carboxylic acid in good yield.

Preparation

To synthesize 2,5-dibromopyridine, follow these steps:
Add 2-amino-5-bromopyridine (13.0 kg) into a water-cooled solution at 10 °C.
Slowly add 47% aqueous hydrogen bromide (37 L) to the mixture.
Introduce liquid bromine (11 L) into the mixture.
Maintain the reaction temperature below 10 °C.
Prepare a solution of NaNO2 (16.1 kg) and H2O (19 L) and add it dropwise to the mixture while keeping the temperature between 0-5 °C.
Stir the reaction mixture for 30 minutes.
Treat the mixture with a solution of NaOH (28.0 kg) in water (30 L) at a controlled rate below 20-25 °C.
Extract the reaction mixture with diethyl ether (3 × 40 L).
Dry the organic layer with anhydrous Na2SO4.
Remove the desiccant by filtration.
Evaporate the resulting filtrate under reduced pressure to dryness.
Suspend the residue in heptane (10 L).
Collect the target product molecule, 2,5-dibromopyridine, by filtration.
Synthesis method of 2,5-dibromopyridine