Water → 4-(3-Hydroxypropylsulfanyl)phenylbenzonitrile

Temperature

80 °C

3-(3-Bromophenylsulfanyl)propane-1-ol (0.49 g) was suspended in acetonitrile (8.5 mL), 4-cyanophenylboronic acid (0.34 g), sodium carbonate (0.42 g), water (1.7 mL) and tetrakis(triphenylphosphine)palladium(0) (0.12 g) were added, and the resulting mixture was stirred at 80° C. for 7 hours. The reaction mixture was cooled to room temperature and then partitioned between ethyl acetate (35 mL) and water (10 mL). The organic layer was washed successively with water (10 mL) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) to give the title compound (0.38 g).

1. temperatureThe reaction mixture was cooled to room temperature
2. custompartitioned between ethyl acetate (35 mL) and water (10 mL)
3. washThe organic layer was washed successively with water (10 mL) and brine (10 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

ORD record

ord-ad5c31d107e24ae6804bfbd2b1c92f9e

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795236B2