Carbon Tetrachloride → 2,4-Dichloro-5-(trichloromethyl)pyridine

To a solution of (4,6-dichloropyridin-3-yl)methanol (7 g, 39 mmol) in CCl4 (200 mL), was added sulfuryl dichloride (120 mL) dropwise with stirring. The resulting solution was heated at reflux overnight. The mixture was concentrated and the pH was adjusted to pH 8 by the addition of NaHCO3 (2N). The resulting solution was extracted with EtOAc (2×100 mL) and the organic layers were combined and dried over Na2SO4. The residue was purified by silica gel column chromatography to afford 1.2 g (12%) of 2,4-dichloro-5-(trichloromethyl)pyridine.

1. temperatureThe resulting solution was heated
2. temperatureat reflux overnight
3. concentrationThe mixture was concentrated
4. additionthe pH was adjusted to pH 8 by the addition of NaHCO3 (2N)
5. extractionThe resulting solution was extracted with EtOAc (2×100 mL)
6. dry with materialdried over Na2SO4
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-33040c7e138f4ba490e102c4c11b75a5

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915253B2