Ethylene Oxide → 2-(6-Bromopyridin-3-yl)ethanol

BuLi (32.2 ml of a 1.6 M solution in hexanes, 52 mmol) added dropwise to a stirred solution of 2,5-dibromopyridine (11.09 g, 46.8 mmol) in Et2O (400 ml) at −78° C. under nitrogen. Upon complete addition the reaction mixture was stirred for 45 min and then a solution of ethylene oxide (6.74 g, 0.14 mol) in THF (70 ml) was added. The reaction mixture was warmed to room temperature, stirred for 1 h and then quenched by addition of NH4Cl solution (sat., 150 ml). The organics were extracted with EtOAc (3×100 ml), washed with brine (100 ml) and dried (MgSO4). The material was concentrated under reduced pressure, whilst simultaneously dry-loading onto silica. The material was purified by column chromatography on silica eluting with Et2O and then EtOAc to give the pure alcohol (3.8 g, 40%).

1. additionUpon complete addition the reaction mixture
2. stirringstirred for 1 h
3. customquenched by addition of NH4Cl solution (sat., 150 ml)
4. extractionThe organics were extracted with EtOAc (3×100 ml)
5. washwashed with brine (100 ml)
6. dry with materialdried (MgSO4)
7. concentrationThe material was concentrated under reduced pressure
8. customwhilst simultaneously dry-loading onto silica
9. customThe material was purified by column chromatography on silica eluting with Et2O

ORD record

ord-f3eef6c20b214f90a1dee85df08a484c

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900209B2