Sodium Hydroxide → 3,5-Bis(4-bromophenyl)isoxazole

HRID 355617

Reaction equation

HRID 355617 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.Cl.[NH2:21]O.[OH-].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[O:18][N:21]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1474381,3-Propanedione, 1,3-bis(4-bromophenyl)-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 122077563,5-Bis(4-bromophenyl)isoxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In a 250 ml round bottom flask, 4 g (10.4 mmol) of [2] was dissolved in 100 ml dry dioxane and heated to reflux, then 3.0 g (43.2 mmol) hydroxylamine hydrogen chloride in 10 ml water and 5 ml (25 mmol) 5N NaOH was then dropped into the refluxing mixture. After 12 hours, the reaction mixture was cooled down to room temperature, and the solvent was removed in vacuo. The product was recrystallized from ethanol. Characterization. Yield: 3.41 g (85%). M.P. 218.5°-219.5° C. 1H NMR (300 MHz, CDCl3, 20° C., δ): 7.78(d, 2H, ArH), 7.74 (d, 2H, Ar'H), 7.66 (d, 2H, ArH), 7.62 (d, 2H, Ar'H), 6.82 (s, 1H, isoxazole proton). EI-MS: 379(M+), 224, 183, 155.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customthe solvent was removed in vacuo
  4. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-d5ce6b5249a445269d9a8e8de2e727ae
Source dataset
uspto-grants-1998_11
Patent number
US05834100

Linked notes

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