Tert-Butyl nitrite → 3,5-Dibromo-2-methylpyridine

HRID 2224348

Reaction equation

HRID 2224348 reaction equation
[Br:1][C:2]1[C:3](N)=[N:4][C:5]([CH3:9])=[C:6]([Br:8])[CH:7]=1.C(ON=O)(C)(C)C>C1COCC1>[Br:8][C:6]1[C:5]([CH3:9])=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=1

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 522994Wisteria sinensis, ext.

Product 1

HCID 6197053,5-Dibromo-2-methylpyridineYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dibromo-6-methyl-pyridin-2-ylamine (2.0 g, 7.5 mmol) in THF (75 mL) was added t-butylnitrite (1.5 mL, 12.6 mmol) and the reaction was heated to reflux for 2 hours. The reaction was concentrated in vacuo and purified by flash chromatography (SiO2, CH2Cl2) to give 52A (0.8 g 42%). HPLC Rt=2.77 min.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe reaction was concentrated in vacuo
  4. custompurified by flash chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-047d0d3583784aa993554947dd91ce01
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Linked notes

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