Imidazole → HCID 59333358, compound

To a solution of 4-bromo-1-fluoro-2-nitrobenzene (1.12 mL; 9.09 mmol; 1 eq) and diisopropylethylamine (1.58 mL; 9.09 mmol; 1 eq;) in anhydrous acetonitrile (80 mL) is added imidazole (620 mg; 9.09 mmol; 1 eq) under argon. The reaction mixture is allowed to stir under reflux for 65 hours until complete consumption of starting material. The crude mixture is concentrated under vacuum and the resulting powder dissolved in ethyl acetate (60 mL). The organic phase is then washed with water (50 mL), brine (50 mL) and dried over sodium sulfate to provide an orange powder after concentration under vacuum. Further purification by flash chromatography on silica gel (ethyl acetate/cyclohexane 9:1) afforded the title compound (1.81 g; 6.7 mmol; 74%) as an orange powder.

1. temperatureunder reflux for 65 hours until complete consumption of starting material
2. concentrationThe crude mixture is concentrated under vacuum
3. dissolutionthe resulting powder dissolved in ethyl acetate (60 mL)
4. washThe organic phase is then washed with water (50 mL), brine (50 mL)
5. dry with materialdried over sodium sulfate
6. customto provide an orange powder
7. concentrationafter concentration under vacuum
8. customFurther purification by flash chromatography on silica gel (ethyl acetate/cyclohexane 9:1)

ORD record

ord-0cf825766bbd4bbdb04d2ff323a205d7

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08513250B2