Thionyl Chloride → 5-(Chloromethyl)-2-methylpyridine

Temperature

0 °C

In a 250 ml round-bottomed flask at room temperature under nitrogen, (6-methyl-3-pyridinyl)methanol (4.32 g, 35.1 mmol, D8) was dissolved in dry dichloromethane (45 ml) to give a yellow solution, which was cooled down to 0° C. Thionyl chloride (3 ml, 41.1 mmol) was then added. The resulting pale-orange mixture was stirred at 0° C. for 15 minutes and at room temperature for 2 hours. The mixture was concentrated in vacuum and the brown residue was partitioned between DCM (150 ml) and saturated NaHCO3 (100 ml). Phases were separated and the organic was washed with saturated NaHCO3 (2×100 ml), dried over Na2SO4, filtered and concentrated to give the desired compound as brown oil (4.26 g), that was used without further purification in the next step.

1. customto give a yellow solution, which
2. concentrationThe mixture was concentrated in vacuum
3. customthe brown residue was partitioned between DCM (150 ml) and saturated NaHCO3 (100 ml)
4. customPhases were separated
5. washthe organic was washed with saturated NaHCO3 (2×100 ml)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-a4ecfe7d74014dffababd7c7c986d542

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173820B2