ChemicalBook CAS DataBase List 2-Bromo-4-nitroimidazole

2-Bromo-4-nitroimidazole synthesis

4synthesis methods

Product Name:2-Bromo-4-nitroimidazole
CAS Number:65902-59-2
Molecular formula:C3H2BrN3O2
Molecular Weight:191.97

2-bromo-4-nitroimidazole is synthesized by dibromination of 4-nitroimidazole followed by selective debromination using in situ reductive deiodination strategy.

6154-30-9 Synthesis

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Yield:65902-59-2 71%

Reaction Conditions:

Stage #1:2,4⁽⁵⁾-dibromo-5⁽⁴⁾-nitroimidazole with tetrabutylammonium borohydride in 1,4-dioxane at 20; for 23 h;Heating / reflux;
Stage #2: with hydrogenchloride in 1,4-dioxane;waterProduct distribution / selectivity;

Steps:

3 Synthesis of 2-bromo-4-nitroimidazole
Example 3 Synthesis of 2-bromo-4-nitroimidazole Into 1,4-dioxane (1 ml) solution of tetra-n-butylammonium borohydride (638 mg) was added dropwise 1,4-dioxane (1 ml) solution of 2,5-dibromo-4-nitroimidazole (89.5 mg) at a room temperature, after being refluxed the reaction mixture for 23 hours, excessive reagents were quenched by adding concentrated hydrochloric acid, then water and ethyl acetate were added. The organic layer was washed with an aqueous solution being saturated with sodium chloride, then dried over anhydrous sodium sulfate, and purified by a thin layer chromatography (developing agent: ethyl acetate) to obtain 2-bromo-4-nitroimidazole (44.9 g, yield: 71%) of white powdery product. ¹H-NMR (DMSO-d₆) δ(ppm): 8.42 (s, 1H), 14. 10 (bs, 1H).

References:

Otsuka Pharmaceutical Company, Limited EP1553088, 2005, A1 Location in patent:Page/Page column 49

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6154-30-9 Synthesis

6154-30-9
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65902-59-2
297 suppliers
$6.00/1g

References