Water → 3-(4-Bromo-2-(methoxycarbonyl)phenoxy)-4-nitropyridine 1-oxide

HRID 335858Notes

Reaction equation

HRID 335858 reaction equation
[Br:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:16]1[CH:17]=[N+:18]([O-:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23].O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][C:16]2[CH:17]=[N+:18]([O-:25])[CH:19]=[CH:20][C:21]=2[N+:22]([O-:24])=[O:23])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 77683Methyl 5-bromosalicylateHCID 5485213-Bromo-4-nitropyridine N-oxide

Product 1

HCID 673828703-(4-Bromo-2-(methoxycarbonyl)phenoxy)-4-nitropyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromosalicylate (5.78 g, 25.00 mmol) in 30 mL of dry THF was added slowly sodium hydride (0.600 g, 25.00 mmol, 60 wt %) and the solution was stirred at rt for 15 minutes. The solvent was evaporated and the residue was dissolved in 10 mL of dry DMF. To this was added 3-bromo-4-nitropyridine 1-oxide (4.38 g, 20.00 mmol) and the reaction mixture was stirred at 50° C. for 4 h and 40° C. overnight. Water was added and the resulting solid was washed with water, filtered and dried under vacuum. Purification of the crude residue by column chromatography (CH2Cl2 to CH2Cl2/EA=10:1 to 5:1 to 3:1 to 1:1 to pure EA) gave 3-(4-bromo-2-(methoxycarbonyl)phenoxy)-4-nitropyridine 1-oxide as a yellow solid.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 10 mL of dry DMF
  3. stirringthe reaction mixture was stirred at 50° C. for 4 h and 40° C. overnight
  4. washthe resulting solid was washed with water
  5. filtrationfiltered
  6. customdried under vacuum
  7. customPurification of the crude residue by column chromatography (CH2Cl2 to CH2Cl2/EA=10:1 to 5:1 to 3:1 to 1:1 to pure EA)

Sources & evidence

ORD record
ord-ab4b32cdd0264c4d8581ddc72b43342a
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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