Sodium Hypochlorite → 3-Chloro-6-fluoro-5-nitro-1H-indazole

HRID 734703Notes

Reaction equation

HRID 734703 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[O-][Cl:15].[Na+]>CCO>[Cl:15][C:6]1[C:5]2[C:9](=[CH:10][C:2]([F:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)[NH:8][N:7]=1

Participants

4

Reactant 2

HCID 23665760Sodium HypochloriteHCID 459336676-Fluoro-5-nitro-1H-indazole

Product 1

HCID 1785264023-Chloro-6-fluoro-5-nitro-1H-indazoleYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Fluoro-5-nitroindazole (850 mg, 4.693 mmol, 1.0 equiv) was dissolved in 20 mL EtOH, NaOCl (10 mL, 164.26 mmol, 35 equiv) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vacuo to remove EtOH was then diluted with EtOAc and water. The phases were separated, and the organic phase was washed once with satd. NaHCO3, and once with satd. NaCl. The organic phase was dried over Na2SO4, filtered, and concentrated en vacuo. The residue was purified by flash chromatography (10-100% EtOAc in Hexanes) to provide 583 mg (58%) of the title compound as a light orange solid. MS (ES+) m/e 216 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated en vacuo
  2. customto remove EtOH
  3. additionwas then diluted with EtOAc and water
  4. customThe phases were separated
  5. washthe organic phase was washed once with satd
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated en vacuo
  9. customThe residue was purified by flash chromatography (10-100% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-29d897b5921c45ba9e4e825bbcfb2fc0
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

Loading…