Hydrochloric Acid → (5-Bromo-3-pyridinyl)methanol

To a suspension of ethyl 5-bromonicotinate (Alfa Aesar, 10.0 g, 43.46 mmol) in anhydrous THF (20 mL) was added dropwise to a slurry of LiAlH4 (1.91 g, 47.81 mmol) in anhydrous THF (200 mL) under argon at −78° C. and the mixture was stirred for 1.5 h at the same temperature, then warmed to r.t. The reaction mixture was added 15 ml of aqueous HCl (1 M) slowly at −78° C., the mixture was then warmed to rt and added anhydrous Na2SO4, stirred for overnight. The resulting mixture was filtered through celite and the solvent was removed under reduced pressure to give crude (5-bromopyridin-3-yl)methanol, which was used in the next step without purification.

1. temperaturethe mixture was then warmed to rt
2. stirringstirred for overnight
3. filtrationThe resulting mixture was filtered through celite
4. customthe solvent was removed under reduced pressure

ORD record

ord-3e8e0ea01c7d469b828fc1d75b737dcb

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299267B2