Tetrahydrofuran → 3-Bromo-5-(bromoacetyl)isoxazole

HRID 1794775Notes

Reaction equation

HRID 1794775 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7](=[O:9])[CH3:8])[O:4][N:3]=1.[Br-:10].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O1CCCC1>O>[Br:1][C:2]1[CH:6]=[C:5]([C:7](=[O:9])[CH2:8][Br:10])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 136269711-(3-Bromo-1,2-oxazol-5-yl)ethan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 136269733-Bromo-5-(bromoacetyl)isoxazoleYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-bromo-5-acetylisoxazole (which was obtained in Example 117) (16.7 g, 87.9 mmol), phenyltrimethylammonium tribromide (33.4 g, 88.8 mmol) and tetrahydrofuran (150 mL) was stirred at ambient temperature for 18 hours, poured into water and extracted with ether. The organic extracts were washed with brine and dried over MgSO4. Evaporation and purification by distillation gave a light yellow oil (8.9 g, 40% yield); 1H NMR (300 MHz, CDCl3) δ 4.40. (s, 3H), 7.10 (s, 1H).

Workup

  1. extractionextracted with ether
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customEvaporation and purification
  5. distillationby distillation

Sources & evidence

ORD record
ord-332846495cc54d3188fe7c8531fab37b
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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