Dimethylformamide → (6-Bromopyridin-2-yl)methanol

Participants

Reaction Conditions

Reaction Steps

n-BuLi (2.5M, 20.0 mL, 50.0 mmol) in tetrahydrofuran (40 mL) was cooled to −78° C. 2,6-Dibromopyridine (11.85 g, 50.0 mmol) in 70 mL tetrahydrofuran was added dropwise while keeping the internal temperature of the reaction below −70° C. The resulting dark green solution stirred for 15 min at this temperature upon which N,N-dimethylformamide (6.0 mL, 78 mmol) was added over a period of 30 seconds. The reaction stirred at −78° C. for 15 min and methanol (50 mL) and acetic acid (3.2 mL) were added. Sodium borohydride (1.89 g, 50.0 mmol) was added last. The reaction was allowed to warm to room temperature. The solution was carefully quenched with sat. ammonium chloride and then extracted with ethyl acetate (2 times). The organic layers were combined and washed with brine, dried over sodium sulfate, filtered, and concentrated. Flash chromatography (25% ethyl acetate/hexanes) gave 2.57 g (27% yield) of the alcohol as a pale yellow oil.

Provenance & Evidence