Tetrabutylammonium borohydride → 2-Bromo-4-nitro-1H-imidazole

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.

1. temperatureafter being refluxed the reaction mixture for 23 hours
2. customexcessive reagents were quenched
3. additionby adding concentrated hydrochloric acid
4. additionwater and ethyl acetate were added
5. washThe organic layer was washed with an aqueous solution
6. dry with materialdried over anhydrous sodium sulfate
7. custompurified by a thin layer chromatography (developing agent: ethyl acetate)

ORD record

ord-c7482cc7090f4fde80d0568d3453a7b8

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07368579B2