Reaction #1528433

Reaction equation

3-Hydroxy-2-nitropyridine

sodium methoxide

bromine

→

material

Yield 97.9%

2-Bromo-5-hydroxy-6-nitropyridine

Yield 97.9%

Solvents

methanol

methanol

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction was stirred at 0° C. for 30 min
2. 2
   Otherwas quenched with glacial AcOH (2.5 mL)
3. 3
   OtherThe solvent was removed in vacuo

Procedure

3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 mL) and a solution of 25% sodium methoxide in methanol (33 mL, 0.13 mole) was added at room temperature. The mixture was stirred for 30 min, then was cooled to 0° C., and bromine (7.2 mL, 0.14 mole) was added slowly. The reaction was stirred at 0° C. for 30 min, then was quenched with glacial AcOH (2.5 mL). The solvent was removed in vacuo to afford material (30 g, 96%), which was used without further purification.

Source