p-Toluenesulfonic acid monohydrate → 3-(4-Bromophenyl)-4-(3-fluoro-4-methylthiophenyl)-5-methylisoxazole

HRID 396825Notes

Reaction equation

HRID 396825 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[C:15]([F:21])[CH:14]=3)[C:11]([CH3:23])(O)[O:10][N:9]=2)=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[C:15]([F:21])[CH:14]=3)=[C:11]([CH3:23])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 227239503-(4-Bromophenyl)4-(3-fluoro-4-methylthiophenyl)-5-methyl-4,5-dihydro-5-isoxazolol

Product 1

HCID 537411813-(4-Bromophenyl)-4-(3-fluoro-4-methylthiophenyl)-5-methylisoxazoleYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-(4-bromophenyl)-4-(3-fluoro-4-methylthiophenyl)-5-methyl-4,5-dihydro-5-isoxazolol (630 mg, 1.59 mmol) and p-toluenesulfonic acid monohydrate (274 mg, 1.59 mmol) in methanol (10 ml) was refluxed for 2 h. The mixture was evaporated, dissolved in ethyl acetate (100 ml), washed with saturated sodium bicarbonate (50 ml×2), and dried over anhydrous sodium sulfate. Removal of solvent gave 583 mg (97%) of the title compound as a pale yellow oil.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe mixture was evaporated
  3. dissolutiondissolved in ethyl acetate (100 ml)
  4. washwashed with saturated sodium bicarbonate (50 ml×2)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-13857c7b5e654adf9247fe13801534f4
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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