Iodoethane → 2,4,5-Tribromo-1-ethyl-1H-imidazole

Temperature

50 °C

To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (50 ml) is added a solution of 2,4,5-tribromoimidazole (15.09 g, 50 mmol) in DMF (30 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., followed by the dropwise addition of iodoethane (8.19 g, 52.5 mmol, 1.05 eq.). The mixture is stirred at rt for 1 hr, and then heated to 50° C. for an additional 8 hr. The reaction mixture is cooled to rt, and poured into ice-water (200 ml). The mixture is extracted with EtOAc (100 ml×3). The combined organic layers are washed with water, brine, dried over anhydrous sodium sulfate, filtered, and solvent evaporated at reduced pressure. The crude product is purified by flash chromatography on silica gel to give the title product. LCMS 330 (M+1).

1. temperaturecooled to 0° C.
2. stirringThe mixture is stirred at rt for 1 hr
3. temperatureheated to 50° C. for an additional 8 hr
4. temperatureThe reaction mixture is cooled to rt
5. extractionThe mixture is extracted with EtOAc (100 ml×3)
6. washThe combined organic layers are washed with water, brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customsolvent evaporated at reduced pressure
10. customThe crude product is purified by flash chromatography on silica gel

ORD record

ord-46dcf18ec7cf41598714200c3bd40942

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728009B1