Phosphorus oxychloride → 3-Chloro-5-nitrobenzo[d]isoxazole

HRID 636041Notes

Reaction equation

HRID 636041 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9](O)[C:8]=2[CH:13]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:11][N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526505HCID 178526505, compound

Product 1

HCID 125912533-Chloro-5-nitrobenzo[d]isoxazole

Conditions

Temperature
152.5 °C

Procedure

A mixture of 5-nitro-1,2-benzisoxazol-3-ol (4.00 g, 0.0220 mol) and phosphorus oxychloride (40.0 mL, 65.8 g, 0.429 mol) is placed in a glass bomb, heated at 150-155° C. for two hours, cooled overnight, concentrated in vacuo, diluted with methylene chloride, and brought to about pH 8 with sodium hydrogen carbonate solution. The phases are separated. The organic phase is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and a methylene chloride/hexanes solution (1:1) gives the title product as an amber oil which is identified by NMR spectral analysis.

Workup

  1. temperaturecooled overnight
  2. concentrationconcentrated in vacuo
  3. additiondiluted with methylene chloride
  4. customThe phases are separated
  5. washThe organic phase is washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a residue

Sources & evidence

ORD record
ord-d6aba79bd53e411ab9f4be6c61199240
Source dataset
uspto-grants-2001_02
Patent number
US06191275B1

Reaction notes

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