Hydrogen Bromide → 2-Bromo-1-(3,5-dimethyl-4-isoxazolyl)ethanone

HRID 633700Notes

Reaction equation

HRID 633700 reaction equation
[CH3:1][C:2]1[C:6]([C:7](=[O:9])[CH3:8])=[C:5]([CH3:10])[O:4][N:3]=1.[BrH:11].BrBr.C([O-])(O)=O.[Na+]>C(O)(=O)C.O>[Br:11][CH2:8][C:7]([C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH3:10])=[O:9]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 24408BromineHCID 516892Sodium BicarbonateHCID 127203171-(3,5-Dimethylisoxazol-4-yl)ethanone

Product 1

HCID 889959652-Bromo-1-(3,5-dimethyl-4-isoxazolyl)ethanoneYield 86.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

400 mg (2.87 mmol) of 1-(3,5-dimethylisoxazol-4-yl)ethanone are dissolved in 20 mL of glacial acetic acid. 1.42 mL (8.62 mmol) of hydrobromic acid and 163 μl (3.16 mmol) of bromine are added to the medium. The reaction mixture is placed under magnetic stirring at room temperature for 2 hours. The solution is diluted with water, basified with saturated aqueous NaHCO3 solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and evaporated to dryness to give 540 mg of 2-bromo-1-(3,5-dimethylisoxazol-4-yl)ethanone, corresponding to the following characteristics:

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-59458792ba7e4e42bdc86c3d66d9f855
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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