Allyl bromide → HCID 13811728, compound

Temperature

-78 °C

In an amount of 24.8 mg of copper(I) iodide was added with 9 ml of diethyl ether and 343.5 μl of 3-bromoquinoline, then added dropwise with 1.6 ml of a 1.57 M solution of n-butyllithium in hexane at −78° C., and stirred at −78° C. for 30 minutes. This reaction mixture was added with 71.4 μl of allyl bromide, stirred at −78° C. for 30 minutes, then warmed to 0° C., added with 20 ml of saturated aqueous ammonium chloride, diluted with 20 ml of ethyl acetate, and successively washed twice with 20 ml of saturated aqueous ammonium chloride and once with 20 ml of saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane to ethyl acetate/hexane (1:1)) to obtain 130 mg of the title compound.

1. stirringstirred at −78° C. for 30 minutes
2. temperaturewarmed to 0° C.
3. washsuccessively washed twice with 20 ml of saturated aqueous ammonium chloride and once with 20 ml of saturated brine
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to ethyl acetate/hexane (1:1))

ORD record

ord-9f99360e1e224cbb92f42dd0b7c7544e

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365174B2