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

Temperature

0 °C

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).

1. extractionThe mixture was extracted with ethyl acetate
2. washwashed with brine
3. customThe combined extracts were separated
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. washeluted with EtOAc/Heptane (v/v, 1:1)
7. concentrationAfter concentration

ORD record

ord-847bfae31d2540e4997179637e97c133

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519134B2