HCID 18470115, compound → HCID 18470302, compound

Temperature

25 °C

To a solution of butyl lithium (2.5M. 3.2 ml) in anhydrous tetrahydrofuran (75 ml) was added triphenylmethylphosphonium bromide (2.86 g) in portions over 10 min. The mixture was stirred at 25° C. for 3 h and a solution of 8-bromo-1-(4-fluorophenyl)octan-1-one (1.20 g) in dry tetrahydrofuran (15 ml) added dropwise over 5 min. After stirring at 25° C. for 1 h, the mixture was heated at reflux for 24 h. The mixture was evaporated under reduced pressure and partitioned between diethyl ether (70 ml) and water (4×30 ml). The organic layer was washed with brine and dried over magnesium sulfate. Removal of the solvent under reduced pressure gave an oil that was chromatographed on silica gel using 5% diethyl ether in hexane. This gave 9-bromo-2-(4-fluorophenyl)-1-nonene (0.75 g). 1H-NMR (CDCl3) δ 1.2-1.55 (8H, m), 1.80 (2H, m), 2.46 (2H, t), 3.39 (2H, t), 5.03 (1H, bs), 5.20 (1H, bs), 7.03 (2H, m) and 7.3-7.45 (2H, m).

1. stirringAfter stirring at 25° C. for 1 h
2. temperaturethe mixture was heated
3. temperatureat reflux for 24 h
4. customThe mixture was evaporated under reduced pressure
5. custompartitioned between diethyl ether (70 ml) and water (4×30 ml)
6. washThe organic layer was washed with brine
7. dry with materialdried over magnesium sulfate
8. customRemoval of the solvent under reduced pressure
9. customgave an oil that
10. customwas chromatographed on silica gel using 5% diethyl ether in hexane

ORD record

ord-cde8b38099d54704a3bb1b90cb9e9fdc

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06417192B1