Bromoacetonitrile → HCID 89854165, compound

Temperature

0 °C

Sodium hydride (631 mg, 16 mmol) was added to a solution of 4-(methylthio)-1H-pyrazole (1500 mg, 13.14 mmol) in anhydrous tetrahydrofuran (30 mL) under nitrogen at 0° C. The reaction mixture was stirred at 0° C. until gas evolution was no longer observed. Bromoacetonitrile (1.005 mL, 14.43 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 18 h. The mixture was poured into a solution of aqueous ammonium chloride (30 mL) and was extracted with ethyl acetate (60 mL×3). The combined organics were dried over sodium sulfate. The residue was filtered through a plug of silica gel which was eluted with ethyl acetate and the filtrate was concentrated under reduced pressure. The crude material was purified via flash chromatography (0-50% ethyl acetate in heptanes) to afford 2-(4-(methylthio)-1H-pyrazol-1-yl)acetonitrile (1460 mg, 72.54%). MS (ES+) (M+H) 154.1; LCMS retention time 0.40 min (Method N).

1. stirringthe reaction mixture was stirred at room temperature for 18 h
2. extractionwas extracted with ethyl acetate (60 mL×3)
3. dry with materialThe combined organics were dried over sodium sulfate
4. filtrationThe residue was filtered through a plug of silica gel which
5. washwas eluted with ethyl acetate
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe crude material was purified via flash chromatography (0-50% ethyl acetate in heptanes)

ORD record

ord-f0d203621ba74515a651027a93dbd2fb

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2