Phosphorus trichloride → HCID 53639934, compound

HRID 342953Notes

Reaction equation

HRID 342953 reaction equation
O[CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.P(Cl)(Cl)[Cl:25]>ClCCl>[Cl:25][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 54050151HCID 54050151, compound

Product 1

HCID 53639934HCID 53639934, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[hydroxy-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (0.89 g) and phosphorous trichloride (0.57 g) in dichloromethane (50 ml) were stirred at 0° C. for 2 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The organic extracts were dried (anhydrous magnesium sulphate), filtered and evaporated to dryness. The crude product was purified by column chromatography on silica eluted with a mixture of petroleum ether/ethyl acetate to give 4-[chloro-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (compound 298, 0.79 g) as a yellow oil: NMR: (CDCl3) 1.1 (4H,m) 1.9(1H,m) 6.9(1H,s) 7.9(1H,m) 8.0(1H,s) 8.25(2H,m).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic extracts were dried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography on silica
  7. washeluted with a mixture of petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-4a4ca7a114e8440395a6278953aa9c96
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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