3,5-Dibromopyridine → 1432621-15-2

Participants

Reaction Conditions

Reaction Steps

To a cooled (−20° C.) solution of 3,5-dibromopyridine (1.2 g, 5.0 mmol) in THF (2 mL) is added a solution of isopropylmagnesium chloride-lithium chloride complex in THF (1.7 M, 2.9 mL, 4.9 mmol). The resultant mixture is stirred warming to −10° C. for 30 min. The mixture is recooled to −20° C. and 3-oxetanone (432 mg, 6.0 mmol) is added. After stirring for 1 h, the reaction is quenched with saturated aqueous ammonium chloride solution and is extracted with EtOAc. The combined organic extracts are washed with water and brine, dried (MgSO4) and concentrated under reduced pressure. Purification by silica gel column (0-10% MeOH in DCM) provided 3-(5-bromo-pyridin-3-yl)-oxetan-3-ol (320 mg).

Provenance & Evidence