Triphenylphosphine → (4-Bromobutyl)cyclohexane

4-Cyclohexyl-1-butanol (5.00 g) was dissolved in methylene chloride (100 ml), triphenylphosphine (9.15 g) and N-bromosuccinimide (6.21 g) were added under ice-cooling, and the mixture was stirred under ice-cooling for 1 hr, and further at room temperature for 3 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. Diethyl ether (100 ml) was added, and the precipitated triphenylphosphine oxide was filtered off. The concentrate of the filtrate was purified by silica gel column chromatography (hexane alone) to give the object product (6.30 g) as a colorless oil.

1. temperaturecooling
2. temperaturecooling for 1 hr
3. washThe reaction mixture was washed with water and saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was evaporated under reduced pressure
6. additionDiethyl ether (100 ml) was added
7. filtrationthe precipitated triphenylphosphine oxide was filtered off
8. concentrationThe concentrate of the filtrate
9. customwas purified by silica gel column chromatography (hexane alone)

ORD record

ord-64aa60c322fe4e9f8404d9f1e53d5762

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129361B2