Bromoacetonitrile → HCID 9880293, compound

Sodium hydride (60% dispersion in oil, 470 mg, 11.8 mmol) was added to a stirred solution of 4-(3,5-dichlorophenoxy)-3,5-diethyl-1H-pyrazole (3 g, 10.5 mmol, Example 3) in dry N,N-dimethylformamide (20 ml) at 0° C. under nitrogen. The mixture was stirred for 5 minutes during which time hydrogen was evolved and then bromoacetonitrile (0.81 ml, 11.6 mmol) was added. The yellow solution turned dark brown and a precipitate formed. Further dry N,N-dimethylformamide (5 ml) was added to aid dissolution and after 45 minutes the reaction mixture was quenched by the addition of water (1 ml). The mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml). The combined organic layers were washed with water (50 ml) and brine (100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with dichloromethane to provide the title compound (3.2 g) as a yellow powder, m.p. 70-72° C.

1. customa precipitate formed
2. customwas quenched by the addition of water (1 ml)
3. customThe mixture was partitioned between water (150 ml) and diethyl ether (2×150 ml)
4. washThe combined organic layers were washed with water (50 ml) and brine (100 ml)
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by flash chromatography on silica gel eluting with dichloromethane

ORD record

ord-2b3d2b6739d14784883bde15f3234179

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07435728B2