Water → 5-Bromo-2-ethoxy-3-nitropyridine

HRID 241051Notes

Reaction equation

HRID 241051 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.N12[CH2:22][CH2:21]CN=C1CCCCC2.[OH2:23]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:23][CH2:21][CH3:22])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 582557825-Bromo-2-ethoxy-3-nitropyridineYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-bromo-2-chloro-3-nitropyridine (100 mg, 0.42 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (315 uL, 2.11 mmol) in ethanol (1 mL) was heated to 50° C. for 50 min and then cooled to rt. Water was added and the resulting aqueous mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with 1 N HCl, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (gradient, 100% hexanes to 90% hexanes:10% ethyl acetate) to provide 5-bromo-2-ethoxy-3-nitropyridine (52.2 mg, 0.211 mmol, 50% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.42 (d, 1H), 8.36 (d, 1H), 4.55 (q, 2H), 1.45 (t, 3H); MS (EI) for C7H7BrN2O3: 246, 248 (M).

Workup

  1. extractionthe resulting aqueous mixture was extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with 1 N HCl
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (gradient, 100% hexanes to 90% hexanes:10% ethyl acetate)

Sources & evidence

ORD record
ord-1e605cc9f1964cbda347f5bdface24e5
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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