Ammonium Chloride → 1-(3-Bromo-5-chloro-pyridin-4-yl)-ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-Bromo-5-chloro-pyridine-4-carbaldehyde (440 mg, 2 mmol) in THF (8 mL) was added methylmagnesium bromide (3M solution in THF, 2 mL, 6 mmol) at −36° C. After 1 h, the resulting mixture was warmed to 0° C., and saturated NH4Cl solution was added. The mixture was extracted with ethyl acetate, and washed with brine. The combined extracts were separated, dried over MgSO4 and concentrated. The residue was passed though a pad of silica gel and eluted with EtOAc/Heptane (v/v, 1:1). After concentration, 370 mg of title compound was obtained without further purification. ESI-MS m/z: 237.8 [M+1]+, Retention time 1.20 min. 1H-NMR (CDCl3, 400 MHz) δ 1.56 (d, J=6.8 Hz, 3H), 5.43 (q, J=6.8 Hz, 1H), 8.40 (1H), 8.52 (s, 1H).

Provenance & Evidence