Hydrochloric Acid → 3-(3-Bromopropyl)benzonitrile

1.5 g (8.56 mmol) of 3-(3-cyanophenyl)propionic acid and 1.19 ml (8.56 mmol) of triethylamine were dissolved in 42 ml of tetrahydrofuran. 0.819 ml (8.56 mmol) of ethyl chloroformate was added to the solution under cooling with ice, and they were stirred for 20 minutes. Precipitates thus formed were removed by the suction filtration. 3 g of ice and 0.648 g (17.12 mmol) of sodium borohydride were added to the filtrate under cooling with ice, and they were stirred for 1 hour. 20 ml of 1 N aqueous hydrogen chloride solution was added to the reaction mixture, and they were stirred at room temperature for one hour. After the treatment with ethyl acetate as the extractant in an ordinary manner, an oily residue was obtained, which was dissolved in 86 ml of dichloromethane. 5.68 g (17.12 mmol) of carbon tetrabromide and 2.69 g (10.27 mmol) of triphenylphosphine were added to the solution, and they were stirred at room temperature for one hour. The reaction mixture was treated with ethyl acetate as the extractant in an ordinary manner to obtain the crude compound, which was purified by the silica gel column chromatography to obtain the title compound.

1. temperatureunder cooling with ice, and they
2. customPrecipitates thus
3. customformed
4. customwere removed by the suction filtration
5. temperatureunder cooling with ice, and they
6. stirringwere stirred for 1 hour
7. stirringwere stirred at room temperature for one hour
8. stirringwere stirred at room temperature for one hour
9. customto obtain the crude compound, which
10. customwas purified by the silica gel column chromatography

ORDレコード

ord-dc5b9b516e2a4e73a4e5cf25ffe34e21

出典データセット

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07396844B1