Hydrochloric Acid → 5-Acetyl-2-bromopyridine

Participants

Reaction Conditions

Reaction Steps

BuLi (32.8 ml of a 1.6 M solution in hexanes, 53 mmol) was added dropwise over 10 min to a stirred solution of 2,5-dibromopyridine (12.44 g, 52.5 mmol) in Et2O (600 ml) at −78° C. under nitrogen. The resulting suspension was stirred at −78° C. for 1 h and then heated with dimethylacetamide (5.86 ml, 63 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h. 1N HCl (100 ml) was added and the organic layer separated. The aqueous layer was extracted with EtOAc (3×100 ml). The combined organic extracts were dried (MgSO4), concentrated under reduced pressure, then taken up in CH2Cl2 (200 ml) and dry loaded onto silica. Column chromatography on silica using 30-40% EtOAc/iso-hexane as eluent gave the ketone (6.0 g, 57%).

Provenance & Evidence