Acetonitrile → 4-((5-Chloropentyl)oxy)benzonitrile

3.0 g (25.2 mmol) of 4-cyanophenol and 3.67 g (27 mmol) of potassium carbonate were sequentially added to 80 ml of acetonitrile, and then 4.67 g (25.2 mmol) of 1-bromo-5-chloropentane was added thereto. Subsequently, the mixture was refluxed for 7 hrs while maintaining the temperature at 80 to 82°, and then cooled to room temperature after stopping heating. The reaction solution was diluted with ethyl acetate, and the organic layer was washed with purified water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from methanol, and then washed with methanol at −10□. The resultant was dried under reduced pressure to obtain 5.09 g (yield: 90.3%) of a title compound (4).

1. temperatureSubsequently, the mixture was refluxed for 7 hrs
2. temperaturewhile maintaining the temperature at 80 to 82°
3. temperatureafter stopping heating
4. washthe organic layer was washed with purified water
5. dry with materialdried over anhydrous magnesium sulfate
6. distillationThe solvent was distilled off under reduced pressure
7. customthe residue was recrystallized from methanol
8. washwashed with methanol at −10□
9. customThe resultant was dried under reduced pressure

ORD record

ord-aebd8371215341d6aa2d9e70c522001c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943646B2