Bromine → 6-Bromo-2-nitropyridin-3-ol

HRID 1782009Notes

Reaction equation

HRID 1782009 reaction equation
[OH:1][C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].[Br:14]Br>CO>[Br:14][C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([N+:8]([O-:10])=[O:9])[N:4]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 270573-Hydroxy-2-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 218738086-Bromo-2-nitropyridin-3-olYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

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 mol) was added at room temperature. The mixture was stirred for 30 minutes, then cooled to 0° C., and bromine (7.2 ml, 0.14 mol) was added slowly. The reaction was then stirred at 0° C. for 30 minutes, 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.

Workup

  1. stirringThe reaction was then stirred at 0° C. for 30 minutes
  2. customwas quenched with glacial AcOH (2.5 ml)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b6144c65f26f4ab9b05a510cb7e2755e
Source dataset
uspto-grants-2009_03
Patent number
US07498326B2

Reaction notes

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