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

HRID 1052518Notes

Reaction equation

HRID 1052518 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.[Na].[CH3:13][CH2:14][OH:15]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([O:15][CH2:14][CH3:13])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 5360545SodiumHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 582557825-Bromo-2-ethoxy-3-nitropyridineYield 77%

Procedure

5-Bromo-2-chloro-3-nitropyridine (1 g, 4.21 mmol) was dissolved in EtOH (5 ml) and a solution of sodium ethoxyde (21% m/v in EtOH, 1.5 ml, 4.63 mmol) was added dropwise. Once the addition was finished, the solvent was evaporated under reduced pressure and water was added tot the residue. The reaction mixture was extracted with dichloromethane (×3). The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. The resulting crude (805 mg, 77% yield) was pure enough to perform the next synthetic step. Purity: 100%

Workup

  1. additionOnce the addition
  2. customthe solvent was evaporated under reduced pressure and water
  3. additionwas added tot the residue
  4. extractionThe reaction mixture was extracted with dichloromethane (×3)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-35d5e2279211495892b4fb9647e9ce2f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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