Water → 5-Bromo-2-(methylthio)pyridine

Temperature

0 °C

Commercially available 2,5-dibromo pyridine (6.01 g, 25.4 mmol) was dissolved in N,N-dimethylformamide (50 mL), and sodium thiomethoxide (2.20 g, 31.4 mmol) was added, followed by stirring at 0° C. for 3.5 hours under nitrogen atmosphere. The reaction solution was brought back to room temperature, water (250 mL) was added, and extraction was carried out with diethyl ether (250 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-5%) to afford the desired compound (4.90 g, yield 94%) as a white solid.

1. customwas brought back to room temperature
2. extractionextraction
3. washThe organic layer was washed with saturated brine
4. dry with materialsubsequently dried over anhydrous magnesium sulfate
5. distillationThe solvent was distilled off under reduced pressure
6. customthe resulting residue was purified
7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=3%-5%)

ORD record

ord-2d4fa8657dc84c41a2c0f5ea609ed0fd

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08415359B2