Carbon tetrabromide → HCID 15752645, compound

A mixture of 2-(cyclohexyloxy)ethanol (0.5 g, 3.47 mmol), carbon tetrabromide (1.49 g, 4.51 mmol), and dichloromethane (6 mL) was placed in a 20 mL scintillation vial with a magnetic stirring bar and cooled on an ice-water bath. Triphenylphosphine (1.18 g, 4.51 mmol) was added in three portions over 5 min with stirring. The mixture was allowed to warm to ambient temperature and progress was monitored with TLC using ethyl acetate:hexanes (1:1) (Rf starting material=0.6, Rf product=0.9). The mixture was concentrated under reduced pressure. Hexanes (5 mL) and ethyl ether (10 mL) were added twice and removed by decanting, leaving an oily residue that was purified by silical gel chromatography using hexanes as eluant. The title compound was obtained as a yellow oil (0.189 g, 26% yield).

1. customwas placed in a 20 mL scintillation vial with a magnetic stirring bar
2. temperaturecooled on an ice-water bath
3. concentrationThe mixture was concentrated under reduced pressure
4. additionHexanes (5 mL) and ethyl ether (10 mL) were added twice
5. customremoved
6. customby decanting
7. customleaving an oily residue that
8. customwas purified by silical gel chromatography

ORD record

ord-3ec40b67f9eb4be2831ba98eb6c38f03

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09163027B2