(3-Bromopropyl)benzene → HCID 69344821, compound

Temperature

-78 °C

According to Scheme 22 Method A: To a solution of 5-bromo-2-methoxypyridine (1 eq, 2.70 mmol, 0.50 g) in THF (4.4 mL) at −78° C. under nitrogen was added dropwise n-butyl lithium (1 eq, 2.5M in hexanes, 2.70 mmol, 1.10 mL). The reaction mixture was stirred at −78° C. for 30 min. and 1-(3-bromopropyl)benzene (1 eq, 2.70 mmol, 0.40 mL) in solution in THF (1 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min. and then allowed to warm to room temperature for 1 hour. The reaction was quenched at 0° C. with water and extracted with Et2O. The organic phase was dried over Na2SO4, filtered and solvent was removed under reduced pressure leaving an orange oil. This residue was purified by flash chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 97.5/2.5), yielding the title compound (0.46 mmol, 0.10 g, 17%) as a colorless semi-solid.

1. stirringThe reaction mixture was stirred at −78° C. for 30 min.
2. temperatureto warm to room temperature for 1 hour
3. customThe reaction was quenched at 0° C. with water
4. extractionextracted with Et2O
5. dry with materialThe organic phase was dried over Na2SO4
6. filtrationfiltered
7. customsolvent was removed under reduced pressure
8. customleaving an orange oil
9. customThis residue was purified by flash chromatography over silicagel (AIT Flashsmart prepacked column SiO2, cyclohexane/AcOEt 97.5/2.5)

ORD record

ord-a911aae4a78845058afec06f7962175b

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399493B2