Phosphorus tribromide → 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole

To a solution of (1-(2-bromoethyl)-3-nitro-1H-pyrazol-5-yl)methanol (4.24 g, 17.0 mmol) in chloroform (100 mL) was cooled to 0° C. was added phosphorus tribromide (4.59 g, 1.6 ml, 17.0 mmol) drop wise via syringe. The resulting solution was warmed to room temperature and stirred for 2 h. The resulting solution was cooled to 0° C. and diluted with dichloromethane (50 ml). The resulting solution was made basic (pH 8.5) with saturated aqueous sodium bicarbonate was (20 mL). The layers were separated, and the aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine (30 mL), dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo and the residue purified by flash chromatography (silica gel, SF40-240 g, 15% to 40% ethyl acetate in hexanes) to give 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole (3.56 g, 67%) as a white solid.

1. temperatureThe resulting solution was cooled to 0° C.
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane (3×50 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationThe resulting mixture was filtered
7. concentrationconcentrated in vacuo
8. customthe residue purified by flash chromatography (silica gel, SF40-240 g, 15% to 40% ethyl acetate in hexanes)

ORD-Eintrag

ord-568b6c27e832472ebdde4dcc01e42122

Quelldatensatz

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08481540B2