Phosphorus trichloride → HCID 53639934, compound

HRID 266506Notes

Reaction equation

HRID 266506 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-596202606d144d0c9c26cd4c3bcb82c2
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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