Water → 5-Bromo-2-isobutoxybenzonitrile

A suspension of sodium hydride (1.64 g, a 60% suspension in mineral oil, 37.5 mmol) in N,N-dimethylformamide (50 mL) was cooled to 0° C. and thereafter 2-methyl-1-propanol (3.47 mL, 37.5 mmol) was added thereto in small portions. The reaction mixture was stirred at room temperature for 20 minutes. The mixture was cooled again to 0° C., 2-fluoro-5-bromobenzonitrile (5.00 g, 25.0 mmol) was added thereto in small portions, and thereafter the reaction mixture was stirred at room temperature for 15 hours. After the reaction was complete, water (100 mL) was added to the reaction mixture, which was then extracted with ethyl acetate (3×100 mL). The organic phases were combined, washed with a saturated aqueous sodium chloride solution (2×50 mL), and thereafter dried over anhydrous sodium sulfate. After removing sodium sulfate by filtration, the solvent was concentrated under reduced pressure. The crude product obtained was purified by silica gel chromatography (hexane/ethyl acetate=9/1) to obtain the title compound (6.04 g). Yield, 95%.

1. temperatureThe mixture was cooled again to 0° C.
2. stirringin small portions, and thereafter the reaction mixture was stirred at room temperature for 15 hours
3. extractionwas then extracted with ethyl acetate (3×100 mL)
4. washwashed with a saturated aqueous sodium chloride solution (2×50 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. customAfter removing sodium sulfate
7. filtrationby filtration
8. concentrationthe solvent was concentrated under reduced pressure
9. customThe crude product obtained
10. customwas purified by silica gel chromatography (hexane/ethyl acetate=9/1)

ORD record

ord-14d33e58103f4828b2ccaa5891e00b82

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952174B2