Cyanuric chloride → 2,4-Dichloro-6-(2,5-dichlorophenyl)-1,3,5-triazine

Temperatur

-78 °C

Alternatively, to a solution of 2,5-dichloro-iodobenzene (3.1 g, 11.4 mmol), hexamethylphosphoramide (6.6 ml) and tetrahydrofuran (20 ml), cooled to −78° C., was added a solution of tert-butyl lithium in pentane (1.7 M, 8.7 ml, 14.8 mmol) over 20 minutes. After stirring at −78° C. for 3 hours, a solution of cyanuric chloride (3.14 g, 17.1 mmol) in tetrahydrofuran (15 ml) was added over 15 minutes. After stirring at −78° C. for 1 hour, the mixture was warmed to −20° C. over 30 minutes. The reaction was quenched by slow addition of hydrochloric acid (1 M, 20 ml). The mixture was diluted with water (50 ml) and extracted with dichloromethane (3×40 ml). The combined extracts were washed with water (2×50 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (3:5) to provide 2,4-dichloro-6-(2,5-dichloro-phenyl)-[1,3,5]triazine (1.98 g, 59% yield).

1. stirringAfter stirring at −78° C. for 1 hour
2. temperaturethe mixture was warmed to −20° C. over 30 minutes
3. customThe reaction was quenched by slow addition of hydrochloric acid (1 M, 20 ml)
4. additionThe mixture was diluted with water (50 ml)
5. extractionextracted with dichloromethane (3×40 ml)
6. washThe combined extracts were washed with water (2×50 ml)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane-hexane (3:5)

ORD-Eintrag

ord-240c6dda1da749f6ac5c75dab4590918

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07618968B2