Methyl iodide → 5-Bromo-2-methoxy-3-nitropyridine

HRID 557534Notes

Reaction equation

HRID 557534 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:12]I>C(Cl)(Cl)Cl.[Al]>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:8][CH3:12])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178418997HCID 178418997, compound

Product 1

HCID 156456645-Bromo-2-methoxy-3-nitropyridineYield 45%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 5359268AluminumSolvent

Procedure

In a 1 L, round-bottomed, single-necked flask equipped with a magnetic stirring bar was placed 5-bromo-3-nitropyridin-2-ol (50.0 g, 0.23 mol) in CHCl3 (500 mL) under nitrogen in the dark (wrapped in aluminum foil.) To this solution was added Ag2CO3 (75.5 g, 0.28 mol) and MeI (142.0 mL, 2.3 mol). After the mixture was stirred for 48 h at room temperature, it was filtered through a pad of Celite, washed with CH2Cl2, and concentrated. The crude mixture was purified by column chromatography (EtOAc:Hexane, 1:4) to give 24.0 g (45%) of 5-bromo-2-methoxy-3-nitropyridine (15) as a solid.

Workup

  1. customIn a 1 L, round-bottomed, single-necked flask equipped with a magnetic stirring bar
  2. filtrationit was filtered through a pad of Celite
  3. washwashed with CH2Cl2
  4. concentrationconcentrated
  5. customThe crude mixture was purified by column chromatography (EtOAc:Hexane, 1:4)

Sources & evidence

ORD record
ord-039ffc365c8744b7b2d6de67ecbd5c10
Source dataset
uspto-grants-2011_11
Patent number
US08058446B2

Reaction notes

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