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

To as solution of (1-(2-bromoethyl)-3-nitro-1H-pyrazol-5-yl)methanol (482 mg, 1.93 mmol) in chloroform (20 mL) was cooled to 0° C. was added phosphorus tribromide (522 mg, 0.18 mL, 1.93 mmol) drop wise via syringe. The resulting solution was warmed to room temperature and stirred for 1 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 (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo to give 1-(2-bromoethyl)-5-(bromomethyl)-3-nitro-1H-pyrazole (469 mg, 78%) as a yellow solid.

1. temperatureThe resulting solution was cooled to 0° C.
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane (3×20 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

ORD record

ord-ff102a4427ff4573a488bc04a45c2110

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481540B2