Hydrogen Bromide → 2-Bromo-5-iodo-3-nitropyridine

HRID 1434641

Reaction equation

HRID 1434641 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](N)=[N:6][CH:7]=1.N([O-])=O.[Na+].[NH4+].[OH-].[BrH:18]>>[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Br:18])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 33844682-Amino-5-iodo-3-nitropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 186197852-Bromo-5-iodo-3-nitropyridineYield 23%

Procedure

5-iodo-3-nitro-2-aminopyridine (5.6 g, 21.1 mmol) and concentrated HBr (60 mL) were stirred at room temperature for ten minutes. Sodium nitrite (11.7 g, 170 mmol) was then slowly added followed by CuBr (3.9 g, 27.2 mmol). Stirring continued overnight. The mixture was poured into 1:1 NH4OH:H2O, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 9:1 hexane:ethyl acetate to yield 5-iodo-3-nitro-2-bromopyridine (1.618 g, 23%) as a colorless solid.

Workup

  1. extractionH2O, extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-68c9d6171e4c4c63aa75cb8747ad4930
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Linked notes

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