Dimethylformamide → (5-Bromopyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Dissolve 2,5-dibromopyridine (10 g, 42 mmol) in toluene (500 mL) and cool to −78° C. Add 2.5M n-butyllithium in hexane (20.3 mL, 50.6 mmol) and stir the mixture for 7 h at the same temperature. Add DMF (4.2 mL, 54.87 mmol) and stir for 1 h. Warm the solution to 0° C. and add sodium borohydride (3.2 g, 84.42 mmol). Stir the mixture at ambient temperature for 3 h. Dilute with EtOAc and saturated aqueous NH4Cl. Separate the layers and extract the aqueous layer three times with EtOAc. Dry over anhydrous Na2SO4, filter and concentrate in vacuo. Recrystallization from hexane/EtOAc (9:1) gives the desired intermediate as a white solid (5.3 g, 66%).

Provenance & Evidence